Methyl 4-amino-3-fluorobenzoate → 4-{2-[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-acetylamino}-3-fluoro-benzoic acid methyl ester

HRID 889379Notes

Reaction equation

HRID 889379 reaction equation
FC1C([O:8][C:9](=O)[CH:10]([C:17]2[N:18]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[N:19]=[C:20]3[CH2:24][CH2:23][CH2:22][C:21]=23)[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=C(F)C(F)=C(F)C=1F.[CH3:37][O:38][C:39](=[O:48])[C:40]1[CH:45]=[CH:44][C:43]([NH2:46])=[C:42]([F:47])[CH:41]=1>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:37][O:38][C:39](=[O:48])[C:40]1[CH:45]=[CH:44][C:43]([NH:46][C:9](=[O:8])[CH:10]([C:17]2[N:18]([C:25]3[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=3)[N:19]=[C:20]3[CH2:24][CH2:23][CH2:22][C:21]=23)[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:42]([F:47])[CH:41]=1

Participants

5

Reactant 2

HCID 11182865Methyl 4-amino-3-fluorobenzoateHCID 86657983[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid pentafluorophenyl ester

Product 1

HCID 673878384-{2-[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-acetylamino}-3-fluoro-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

In analogy to the procedure described in example 4.3, [2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid pentafluorophenyl ester (example 4.2) was reacted with 4-amino-3-fluoro-benzoic acid methyl ester (CAS Reg. No. 185629-32-7) in the presence of DMAP in DMF to give the title compound as colorless oil. MS: m/e=510.2 [M+H+].

Sources & evidence

ORD record
ord-b8637f3c1a0940558ca419c0740ea039
Source dataset
uspto-grants-2012_08
Patent number
US08252826B2

Reaction notes

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