5-Chloro-3-methoxy-l -phenyl

Chloro-5-methoxy-6-phenylpyrazine 5-Chloro-3-methoxy-l-phenyl-2(17/)-pyrazinone... 

Chloro-3-methoxy-6-methoxymethyl-1 -phenyl-2n //)-pyrazinone 5-Chloro-6-methoxy methyl-1,3-diphenyl-20 //)-pyrazinone 2-Chloro-6-methoxy-3-methyl-5-phenylpyrazine 2-Chloro-6-methoxy-5-methyl-3-phenylpyrazine 5-Chloro-3-methoxy-6-methyl-l-phenyl-2( 1 //t-pvTa/ini iie... 

Chloro-3-dimethylaminosulfonyloxy- 1972 5-(Chloro-dipyridin-palladio)-3-phenyl-1874, 1935 5-Chloromercuri-3-(2-methyl-1 -propenyl)- 1736 5-Chloromercuri-3-phenyl- 1736, 1935 5-Chloro-3-methoxy- 1870, 1932 5-Chloro-3-methoxycarbonyl- 1871 7-Chloro-l-methyl- 7967, 1968... 

Azido-7-chloro-3-methyl-l, 8-naphthyridine 2-Azido-7-chloro-4-methyl-1,8-naphthyridine 2-Azido-7-chloro-5-methyl-1,8-naphthyridine 2- Azido-7-chloro-6-methyl-1,8-naphthyridine 2-Azido-7-chloro-1,8-naphthyridine 2-Azido-7-chloro-3-phenyl-1,8-naphthyridine 2-Azido-7-chloro-4-phenyl-1,8-naphthyridine 2-Azido-7-chloro-5-phenyl-1,8-naphthyridine 2-Azido-7-chloro-6-phenyl-1,8-naphthyridine 2-Azido-4-chloro-3,5,7-trimethyl-1,8-naphthyridine 2-Azido-5,7-dimethyl-1,8-naphthyridine 2-Azido-7-ethoxy-3-methyl-1,8-naphthyridine 2-Azido-7-ethoxy-4-methyl-1,8-naphthyridine 2-Azido-7-ethoxy-5-methyl-1,8-naphthyridine 2-Azido-7-ethoxy-6-methyl-1,8-naphthyridine 2-Azido-7-ethoxy-1,8-naphthyridine 2-Azido-7-ethoxy-3-phenyl-l, 8-naphthyridine 2-Azido-7-ethoxy-4-phenyl-1,8-naphthyridine 2-Azido-7-ethoxy-5-phenyl-1,8-naphthyridine 2-Azido-7-ethoxy-6-phenyl-1,8-naphthyridine 2-Azido-7-methoxy-3-phenyl-l, 8-naphthyridine 7-Azido-3-methyl-l,8-naphthyridin-2-amine 7-Azido-4-methyl-l,8-naphthyridin-2-amine 7-Azido-5-methyl-l,8-naphthyridin-2-amine 7-Azido-6-methyl-l,8-naphthyridin-2-amine 2-Azido-5-methyl-l,8-naphthyridine 2- Azido-6-methyl-1,8-naphthyridine... 

The following alkoxypyrazines have been prepared from the corresponding dichloropyrazines and alkoxide ions 2,3-dimethoxy-5,6-dimethyl(and diphenyl) (797) 2,3-dibenzyloxy (sodium benzyl oxide in benzyl alcohol at reflux for 24 hours (883)] [but 23-dichloropyrazine with sodium hydride and benzyl alcohol in xylene gave l,4-dibenzyl-2,3-dioxo-l,2,3,4-tetrahydropyrazine)(988)] 2-chloro-5-methoxy (838) 2,5-diethoxy-3,6-dimethyl (872) 2methanolic sodium methoxide refluxed for 2 h) 2,5-dimethoxy-3-phenyl (817) 2-chloro-5-methoxy(and ethoxy)-3,6-diphenyl (817) 2,5-dimethoxy-3,6-dimethyl (and diisopropyl) (844) 2,5-dimethoxy-3-isopropyl-6-methyl (methanolic potassium methoxide at reflux for 6 days) (844) 2(5)-s-butyl-3-chloro-6-ethoxy-5(2)-isobutyl (93) 2-chloro-6-methoxy (838, 883) 2,6-dimethoxy (reflux for 8h) (832) 2,6-diethoxy (reflux for 14 h) (883) 2-benzyloxy-6-chloro (1 equiv. of sodium hydride and benzyl alcohol in benzene at reflux) (832) 2,6-dibenzyloxy (5 equiv. of sodium benzyloxide in benzene at reflux gave 70%) (832) and 3,5-dimethoxy-2-methyl (535). 

Chloro-3-hydroxy-5-methyl[ 1,1 -biphenyl]-2-yl)ethanone, 1188 l-(4 -Chloro-4-methoxy[l,l -biphenyl]-2-yl)ethanone, 1188 l-[4-Chloro-2-(phenylmethoxy)phenyl]ethanone, 1106... 

Typical experimental procednre for BMS-204352 To a solution of l,4-diazabicyclo[2.2.2]octane (35 mg, 0.31 mmol) in THF (1 mL) was added 3-(5-chloro-2-methoxy-phenyl)-6-trifluoro-methyl-l,3-dihydro-indol-2-one (48 mg, 0.14 mmol) at 20°C. The mixture was stirred for 30 minutes, and then the temperature was cooled to —78 °C. lV-fluoro-2-naphtoylquininium tetrafluoro-borate (F-2NaphtQN-Bp4) (99.4 mg, 0.17 mmol) was dissolved in a mixture of 3-mL CH3CN/4=mL CH2Cl2and added over a period of 1 hour. The mixture was stirred overnight during that time temperature rise from -78 °C to 0°C and then quenched with 8mL of water. The aqueous phase was extracted with... 

Catalytic asymmetric methylation of 6,7-dichloro-5-methoxy-2-phenyl-l-indanone with methyl chloride in 50% sodium hydroxide/toluene using M-(p-trifluoro-methylbenzyDcinchoninium bromide as chiral phase transfer catalyst produces (S)-(+)-6,7-dichloro-5-methoxy-2-methyl-2--phenyl-l-indanone in 94% ee and 95% yield. Under similar conditions, via an asymmetric modification of the Robinson annulation enqploying 1,3-dichloro-2-butene (Wichterle reagent) as a methyl vinyl ketone surrogate, 6,7 dichloro-5-methoxy 2-propyl-l-indanone is alkylated to (S)-(+)-6,7-dichloro-2-(3-chloro-2-butenyl)-2,3 dihydroxy-5-methoxy-2-propyl-l-inden-l-one in 92% ee and 99% yield. Kinetic and mechanistic studies provide evidence for an intermediate dimeric catalyst species and subsequent formation of a tight ion pair between catalyst and substrate. 

In alkaline media, 3-halogeno compounds appear to be less stable 3-chloro-5-phenyl-l,2,4-thiadiazole is decomposed completely by 1 Jf-alcoholic potassium hydroxide and by hydrazine.178 Nucleophilic substitution of the 3-halogen atom by alkoxy groups can be achieved, however, by means of sodium alkoxide in the appropriate alcohol 3-methoxy-, 3-benzyloxy-, and 3-(2 -hydroxyethoxy)-5-phenyl-l,2,4-thiadiazole are obtainable by this route in good yield.178... 

Reaction of 9-hydroxy-2-methyl-6-phenyl-l,2,3,6,7,llh-hexahydro-4//-pyrazino[2,l-a]isoquinoline, prepared from its 9-methoxy derivative in 48% HBr, with 5-chloro-l-phenyl-l//-tetrazole in the presence of K2C03 in DMSO yielded the 9-(l-phenyl-l//-tetrazol-5-yloxy) derivative, which then gave its 9-unsubstituted derivative by hydrogenation over 5% Pd-C (88USP4782058). 

Many amides have been prepared from pyrazinecarboxylic acid chlorides some are listed below with the relevant amines and references 2-chlorocarbonyl [MeNHj/ EtOAc (138) Me NH/EtOAc (138) BujNH etc/EtOAc (138) aniline/EtOAc (138, 1335) other aromatic and heterocyclic amines/EtOAc (138) sulfanilamide/ pyridine (1336) p-(2 -aminoethyl)benzenesulfonamide (1385) p-anisidine/benzene (1334) 4-hydroxypiperidine/benzene chloroform (1386) morpholine/DMF/20° (1387) 2-aminopyrimidine/benzene (1388) glycine/NaOH/ether (1201, cf. 1333, 1360)] 2-chlorocarbonyl-5-methyl [MeNHj/benzene (1337) MejNH/benzene (1337) 4-phenylpiperazine or diethanolamine/benzene-chloroform (1386) 2-chlorocarbonyl-3-phenyl (6-aminopenicillanic acid) (1024) 2-chloro-3-chloro-carbonyl (morpholine/benzene) (838) 2-chloro-5-chlorocarbonyl (NH4OH) (839) 2-chloro-6-chlorocarbonyl (Et2NH/benzene) (870, 1389) 2-chlorocarbonyl-5-hydroxy (aniline/benzene) (1055) 2-chlorocarbonyl-3-methoxy (morpholine/ benzene) (867) 2-chlorocarbonyl-5-methoxy (morpholine/benzene-chloroform) (1386) and 2-(l -chlorocarbonylethyI) (morpholine/benzene) (364). 

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