Cyclohexylamine → [Rac]-2-[2-(4-chloro-phenyl)-5,6-difluoro-2h-indazol-3-yl]-2,n-dicyclohexyl-acetamide

HRID 1678651Notes

Reaction equation

HRID 1678651 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.[CH:33]1([NH2:39])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>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[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)[C:18]([NH:39][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[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 7965CyclohexylamineHCID 24386Thionyl ChlorideHCID 67131115[rac]-[2-(4-chloro-phenyl)-5,6-difluoro-2H-indazol-3-yl]-cyclohexyl-acetic acid

Product 1

HCID 45110777[Rac]-2-[2-(4-chloro-phenyl)-5,6-difluoro-2h-indazol-3-yl]-2,n-dicyclohexyl-acetamide

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 was converted into the corresponding acid chloride with thionyl chloride which subsequently reacted with cyclohexylamine (CAS Reg. No. 108-91-8) in the presence of DMAP to give the title compound as off-white solid. MS: m/e=486.4 [M+H+].

Sources & evidence

ORD record
ord-7f975734f5d64e468edbaccf19eebc7c
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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