2-Butanol, 1-methoxy- → 5-(4-Chloro-phenyl)-n-((1r,2r)-2-hydroxy-cyclohexyl)-6-(1-methoxymethyl-propoxy)-nicotinamide

HRID 1929854Notes

Reaction equation

HRID 1929854 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[C:7](Cl)=[N:6][CH:5]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.[CH3:23][O:24][CH2:25][CH:26]([OH:29])[CH2:27][CH3:28].[NH2:30][C@@H:31]1[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]1[OH:37]>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:8]2[C:7]([O:29][CH:26]([CH2:25][O:24][CH3:23])[CH2:27][CH3:28])=[N:6][CH:5]=[C:4]([CH:9]=2)[C:3]([NH:30][C@@H:31]2[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]2[OH:37])=[O:12])=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 408952-Butanol, 1-methoxy-HCID 742994-Chlorophenylboronic acidHCID 735777(1R,2R)-2-AminocyclohexanolHCID 2764313Methyl 5-bromo-6-chloronicotinate

Product 1

HCID 675048615-(4-Chloro-phenyl)-n-((1r,2r)-2-hydroxy-cyclohexyl)-6-(1-methoxymethyl-propoxy)-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 43, using 5-bromo-6-chloro-nicotinic acid methyl ester, 4-chlorophenyl-boronic acid (commercially available), rac-1-methoxy-2-butanol (commercially available), and (1R,2R)-2-amino-cyclohexanol (commercially available) as starting materials. MS (ISP): 433.3, 435.3 (M+H+).

Workup

  1. customdescribed for the preparation of Example 43

Sources & evidence

ORD record
ord-1b761709867148c5a242282d69e0750c
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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