4-Chlorophenylboronic acid → 5-(4-Chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-((S)-2-methoxy-propoxy)-nicotinamide

HRID 1159253Notes

Reaction equation

HRID 1159253 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([OH:11])=O)[CH:5]=[N:6][C:7]=1Cl.[CH3:12][O:13][C@@H:14]([CH3:17])[CH2:15][OH:16].[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.[NH2:28][C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]1[OH:35]>>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[C:7]([O:16][CH2:15][C@@H:14]([O:13][CH3:12])[CH3:17])=[N:6][CH:5]=[C:4]([CH:3]=2)[C:9]([NH:28][C@@H:29]2[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]2[OH:35])=[O:11])=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 742994-Chlorophenylboronic acidHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 6424022-Methoxy-1-propanol, (2S)-HCID 735777(1R,2R)-2-Aminocyclohexanol

Product 1

HCID 675051405-(4-Chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-((S)-2-methoxy-propoxy)-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 31, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, (S)-(+)-2-methoxypropanol (commercially available), 4-chlorophenyl-boronic acid (commercially available), and (1R,2R)-2-amino-cyclohexanol (commercially available) as starting materials. MS (ISP): 419.2 (M+H+).

Workup

  1. customdescribed for the preparation of Example 31

Sources & evidence

ORD record
ord-ec5073c1fc074c58a032353a184906a6
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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