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

HRID 1159323Notes

Reaction equation

HRID 1159323 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:27])[C:13]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[C:16](Cl)=[N:15][CH:14]=1.[NH2:28][C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]1[OH:35]>>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([C:17]2[C:16]([CH2:2][CH2:1][C:3]3[CH:8]=[CH:7][C:6]([F:9])=[CH:5][N:4]=3)=[N:15][CH:14]=[C:13]([CH:18]=2)[C:12]([NH:28][C@@H:29]2[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]2[OH:35])=[O:27])=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 735777(1R,2R)-2-AminocyclohexanolHCID 447549262-Ethynyl-5-fluoropyridineHCID 73013037HCID 73013037, compound

Product 1

HCID 247976185-(4-Chloro-phenyl)-6-[2-(5-fluoro-pyridin-2-yl)-ethyl]-N-((1R,2R)-2-hydroxy-cyclohexyl)-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-chloro-phenyl)-nicotinic acid methyl ester, and (1R,2R)-2-amino-cyclohexanol (commercially available) as starting materials, LC at 215 nm; Rt 4.12: 99%, m/z (ES+): 454.5 (M+H).

Workup

  1. customdescribed for the preparation of Example 140

Sources & evidence

ORD record
ord-5709ae72553a47ce86f7b4e331f865bc
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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