4- amino-5-chloro-N- l- 3-

Chemical Name Benzamide, 4-amino-5-chloro-N-(l-(3-(4-fluorophenoxy) propyl)-3-methoxy-4-piperidinyl)-2-methoxy-, monohydrate, cis-... 

To a solution of 4-amino-5-chloro-2-methoxybenzoic acid (20.2 g) in methyl isobutylketone (250 ml) and triethyl amine (15.3 ml) was slowly dropped ethyl chloroformate (9.6 ml). The reaction mixture was stirred for 30 min at room temperature. To the formed mixed anhydride was then added l-[3-(4-fluorophenoxy)-propyl]-3-methoxy-4-piperidinamine (28.2 g) and the reaction mixture was stirred for 2 hours at room temperature. Subsequently, the reaction mixture was washed with water (80 ml) and a NaOH solution (6.5% w/v, 50 ml). The organic layer was warmed to 65°C and methanol (50 ml) and water (8.5 ml) were added. The solution was cooled slowly and stirred for 2 days during which crystallisation occurred, yielding benzamide, 4-amino-5-chloro-N-(l-(3-(4-fluorophenoxy)propyl)-3-methoxy-4-piperidinyl)-2-methoxy-, monohydrate, cis- (Cisapride) having a cis/trans ratio higher than 99/1. 

S (Z)]]-7-[(2-amino-2-carboxyethyl)thio]-2-[[(2,2-dimethylcyclopropyl)carbonyl]amino]-2-heptanoic acid cjs-4-amino-5-chloro-N-[l-[3-(p-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-o-anisamide cis-4-amino-5-chloro-N-[l-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxybenz amide [l-amino-3-[[[2-[(diaminomethylene)amino]-4-thiazolyljmethyl] thio]propylidene]sulfamide 2-amino- l,9-dihydro-9-[(2-hydroxyethoxy)methyl]-6H-purin-6-one l-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(2,3-dihydro-l,4-benzodioxin-2-yl)carbonyl]piperazine... 

Internal standard cis-4-amino-5-chloro-n- l-[5-(4-fluorophenoxy)pentyl]-3-methoxy-4-pi-peridinyl -2-methoxybenzamide monohydrate (3.8)... 

ACh acetylcholine 2-methyl-5>Hl 2-methyl-5-hydroxytryptamine 3>chloro-PBG l-(3-chloro-phenyl)-biguanide 5-HT 5-hydroigrtryptamine Azasetron N-(l-azabicyclo[2.2.2.]oct-3-yl)-6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-l,4 -benzoxazine-8-carboxamide Batanopride 4-amino-5-chloro-N-[2-([Pg.258]

Exo-N-1-butyl-l-azabicyclo [3.3.1]-nonan-3-yl]-4-amino-5-chloro-2-methoxy-benzamide, HCl... 

Amino-2-chloro-6,7-dimethoxyquinazoline (140 g) and N-(l,4-benzodioxan-2-carbonyl)piperazine (150 g) were stirred together under reflux in n-butanol (2 L) for 3.5 hours. The mixture was then cooled to 80°C, the solid product collected, washed with cold n-butanol (2 times 250 ml), and dried. The crude product was dissolved in hot (80°C) dimethylformamide (530 ml) and water (130 ml), filtered, concentrated in vacuo to about 300 ml, then cooled and ether (1.8 L) added. The solid so obtained was collected and washed with ether to give 4-amino-2-[4-(l,4-benzodioxan-2-carbonyl)piperazin-l-yl]-6,7-dimethoxyquinazoline hydrochloride (215 g), melting point 289°C-290°C. Mesylate may be prepared by usual method from hydrochloride with methylsulphonic acid. 

A new efficient procedure has been proposed for the synthesis of 3-aryl-5-amino-l//-pyrazoles by reaction of a-chloro-/ -arylacrylonitriles with hydrazine hydrate <2004RJ01518>. Reaction of 2-(3,3-dicyano-2-propenylidene)-4,4,5,5-tetra-methyl-l,3-dioxolane 641 with hydrazine afforded 3-(2-hydroxy-l,l,2-trimethylpropoxy)pyrazole 642 (Equation 134) <2003RJ01016>. Treatment of ethyl 3,3-dicyano-2-methoxyacrylate with alkyl, aryl, heterocyclic, and sulfonyl hydrazines led to the synthesis of N-l-substituted 3-acyM-cyano-5-aminopyrazoles, which are versatile intermediates for the synthesis of many biologically active scaffolds <2006TL5797>. 2-Hydrazinothiazol-4(5//)-one reacted with a variety of cinnamonitrile derivatives and activated acrylonitriles to yield annelated pyrazolopyrano[2,3-rf thiazole <1998JCM730>. 

Fig. 7-6). Two unichiral amides which have been known capable of this reaction are 1-phenylethylamine [15] and l-(l-naphthyl)ethylamine [16]. Marfey s reagent [N-a-(2,4-dinitro-5-fluorophenyl)-L-alaninamide] was introduced as a reagent to deriva-tize amino acids with cyclopentane, tetrahydroisoquinoline or tetraline structures [17]. Simple chiral alcohols such as 2-octanol can also be used to derivatize acids such as 2-chloro-3-phenylmethoxypropionic acid [18]. 

Both 3-amino-N-ethylcarbazole and l,4-diethoxy-2-amino-5-benzoylamino-benzene are suitable aromatic amines. Chloranil may also be replaced by 2,5-di-chloro-3,6-bisacetylamino-l,4-benzoquinone to react with appropriately substituted o-alkoxyanilines. 

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