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

HRID 1678654Notes

Reaction equation

HRID 1678654 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.[CH2:33]([O:35][C:36](=[O:49])[C:37]([O:40][C:41]1[CH:46]=[CH:45][C:44]([NH2:47])=[C:43]([F:48])[CH:42]=1)([CH3:39])[CH3:38])[CH3:34]>CN(C1C=CN=CC=1)C>[CH2:33]([O:35][C:36](=[O:49])[C:37]([O:40][C:41]1[CH:46]=[CH:45][C:44]([NH:47][C:18](=[O:19])[CH:17]([C:16]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[N:9]=[C:10]3[C:15]=2[CH:14]=[C:13]([F:27])[C:12]([F:28])=[CH:11]3)[CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)=[C:43]([F:48])[CH:42]=1)([CH3:39])[CH3:38])[CH3:34]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 671309762-(4-Amino-3-fluoro-phenoxy)-2-methyl-propionic acid ethyl esterHCID 67131115[rac]-[2-(4-chloro-phenyl)-5,6-difluoro-2H-indazol-3-yl]-cyclohexyl-acetic acid

Product 1

HCID 45110917[Rac]-2-(4-{2-[2-(4-chloro-phenyl)-5,6-difluoro-2h-indazol-3-yl]-2-cyclohexyl-acetylamino}-3-fluoro-phenoxy)-2-methyl-propionic acid ethyl ester

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 2-(4-amino-3-fluoro-phenoxy)-2-methyl-propionic acid ethyl ester in the presence of DMAP to give the title compound as brown solid. MS: m/e=628.3 [M+H+].

Sources & evidence

ORD record
ord-3f38f376a36d427fa7a3b5990b31f24d
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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