Thionyl Chloride → [Rac]-4-{2-[2-(4-chloro-phenyl)-5,6-difluoro-2h-indazol-3-yl]-2-cyclohexyl-acetylamino}-3-fluoro-benzoic acid

HRID 1678662Notes

Reaction equation

HRID 1678662 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([CH:17]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:18](O)=[O:19])=[C:15]3[C:10]([CH:11]=[C:12]([F:28])[C:13]([F:27])=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C([O:35][C:36](=[O:45])[C:37]1[CH:42]=[CH:41][C:40]([NH2:43])=[C:39]([F:44])[CH:38]=1)C>CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([CH:17]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:18]([NH:43][C:40]3[CH:41]=[CH:42][C:37]([C:36]([OH:35])=[O:45])=[CH:38][C:39]=3[F:44])=[O:19])=[C:15]3[C:10]([CH:11]=[C:12]([F:28])[C:13]([F:27])=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 20536493Ethyl 4-amino-3-fluorobenzoateHCID 67131115[rac]-[2-(4-chloro-phenyl)-5,6-difluoro-2H-indazol-3-yl]-cyclohexyl-acetic acid

Product 1

HCID 45111058[Rac]-4-{2-[2-(4-chloro-phenyl)-5,6-difluoro-2h-indazol-3-yl]-2-cyclohexyl-acetylamino}-3-fluoro-benzoic acid

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In analogy to the procedure described in example 6, [rac]-[2-(4-chloro-phenyl)-5,6-difluoro-2H-indazol-3-yl]-cyclohexyl-acetic acid (example 24.7) was converted into the corresponding acid chloride with thionyl chloride which subsequently reacted with 4-amino-3-fluoro-benzoic acid ethyl ester (CAS Reg. No. 73792-12-8) in the presence of DMAP to give the title compound as yellow liquid. MS: m/e=570.2 [M+H+].

Sources & evidence

ORD record
ord-3065990075454714bcf562ef55981095
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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