(1R,2R)-2-Aminocyclohexanol → N-((1R,2R)-2-Hydroxy-cyclohexyl)-6-[2-(3-methyl-3H-imidazol-4-yl)-ethyl]-5-(4-trifluoromethyl-phenyl)-nicotinamide

HRID 1929926Notes

Reaction equation

HRID 1929926 reaction equation
[C:1]([C:3]1[N:7]([CH3:8])[CH:6]=[N:5][CH:4]=1)#[CH:2].CO[C:11](=[O:29])[C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[C:15](Cl)=[N:14][CH:13]=1.[NH2:30][C@@H:31]1[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]1[OH:37]>>[OH:37][C@@H:32]1[CH2:33][CH2:34][CH2:35][CH2:36][C@H:31]1[NH:30][C:11](=[O:29])[C:12]1[CH:17]=[C:16]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:22][CH:23]=2)[C:15]([CH2:2][CH2:1][C:3]2[N:7]([CH3:8])[CH:6]=[N:5][CH:4]=2)=[N:14][CH:13]=1

Participants

4

Reactant 3

HCID 735777(1R,2R)-2-AminocyclohexanolHCID 33331065-Ethynyl-1-methyl-1H-imidazoleHCID 866195756-Chloro-5-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester

Product 1

HCID 24857346N-((1R,2R)-2-Hydroxy-cyclohexyl)-6-[2-(3-methyl-3H-imidazol-4-yl)-ethyl]-5-(4-trifluoromethyl-phenyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 140, using 5-ethynyl-1-methyl-1H-imidazole (CAN 71759-92-7), 6-chloro-5-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester, and (1R,2R)-2-amino-cyclohexanol (commercially available) as starting materials, LC at 215 nm; Rt 3.11: 100%, m/z (ES+): 473.5 (M+H).

Workup

  1. customdescribed for the preparation of Example 140

Sources & evidence

ORD record
ord-2374145f33d74dd19def9930eeb1645e
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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