(1R,2R)-2-Aminocyclohexanol → 6-[2-(5-Fluoro-pyridin-2-yl)-ethyl]-N-((1R,2R)-2-hydroxy-cyclohexyl)-5-(4-trifluoromethyl-phenyl)-nicotinamide

HRID 1929928Notes

Reaction equation

HRID 1929928 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][N:4]=1)#[CH:2].CO[C:12](=[O:30])[C:13]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[C:16](Cl)=[N:15][CH:14]=1.[NH2:31][C@@H:32]1[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]1[OH:38]>>[F:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH2:2][C:16]2[C:17]([C:19]3[CH:20]=[CH:21][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:23][CH:24]=3)=[CH:18][C:13]([C:12]([NH:31][C@@H:32]3[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]3[OH:38])=[O:30])=[CH:14][N:15]=2)=[N:4][CH:5]=1

Participants

4

Reactant 3

HCID 735777(1R,2R)-2-AminocyclohexanolHCID 447549262-Ethynyl-5-fluoropyridineHCID 866195756-Chloro-5-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester

Product 1

HCID 247976196-[2-(5-Fluoro-pyridin-2-yl)-ethyl]-N-((1R,2R)-2-hydroxy-cyclohexyl)-5-(4-trifluoromethyl-phenyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 140, using 2-ethynyl-5-fluoro-pyridine (CAN 884494-34-2), 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 4.26: 95%, m/z (ES+): 488.5 (M+H).

Workup

  1. customdescribed for the preparation of Example 140

Sources & evidence

ORD record
ord-c40b067ec86a415b9717b44e629f9a2c
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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