Thionyl Chloride → [Rac]-1-(4-{2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2h-indazol-3-yl]-2-cyclohexyl-acetylamino}-3-fluoro-phenoxy)-cyclopropanecarboxylic acid methyl ester

HRID 1678637Notes

Reaction equation

HRID 1678637 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]([CH2:11][CH2:12][CH2:13][CH2:14]3)=[N:9]2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:31][O:32][C:33]([C:35]1([O:38][C:39]2[CH:44]=[CH:43][C:42]([NH2:45])=[C:41]([F:46])[CH:40]=2)[CH2:37][CH2:36]1)=[O:34]>CN(C1C=CN=CC=1)C>[CH3:31][O:32][C:33]([C:35]1([O:38][C:39]2[CH:44]=[CH:43][C:42]([NH:45][C:18](=[O:19])[CH:17]([C:16]3[N:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[N:9]=[C:10]4[C:15]=3[CH2:14][CH2:13][CH2:12][CH2:11]4)[CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[C:41]([F:46])[CH:40]=2)[CH2:37][CH2:36]1)=[O:34]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 67131112[2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acidHCID 671311211-(4-Amino-3-fluoro-phenoxy)-cyclopropanecarboxylic acid methyl ester

Product 1

HCID 45110643[Rac]-1-(4-{2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2h-indazol-3-yl]-2-cyclohexyl-acetylamino}-3-fluoro-phenoxy)-cyclopropanecarboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In analogy to the procedure described in example 6, [2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid (example 5.1) was converted into the corresponding acid chloride with thionyl chloride which subsequently reacted with 1-(4-amino-3-fluoro-phenoxy)-cyclopropanecarboxylic acid methyl ester in the presence of DMAP to give the title compound as yellow oil. MS: m/e=580.4 [M+H+].

Sources & evidence

ORD record
ord-8ed74c0e5dcc4667bb25625271858e2e
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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