2,4-Difluoroaniline → [Rac]-2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2h-indazol-3-yl]-2-cyclohexyl-n-(2,4-difluoro-phenyl)-acetamide

HRID 1678633Notes

Reaction equation

HRID 1678633 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.[F:31][C:32]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:33]=1[NH2:34]>CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[CH:4][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:34][C:33]3[CH:35]=[CH:36][C:37]([F:39])=[CH:38][C:32]=3[F:31])=[O:19])=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 97092,4-DifluoroanilineHCID 24386Thionyl ChlorideHCID 67131112[2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid

Product 1

HCID 45110642[Rac]-2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2h-indazol-3-yl]-2-cyclohexyl-n-(2,4-difluoro-phenyl)-acetamide

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 2,4-difluoroaniline (CAS Reg. No. 367-25-9) in the presence of DMAP to give [rac]-2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-N-(2,4-difluoro-phenyl)-acetamide as yellow oil. MS: m/e=484.3 [M+H+].

Sources & evidence

ORD record
ord-a8e34341c8144eae8fa7ce679cdc55cc
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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