4-(2-Ethoxycarbonylethyl)benzeneboronic acid → 3-{4-[2-Cyclopropylmethoxy-5-((1R,2R)-2-hydroxy-cyclohexylcarbamoyl)-pyridin-3-yl]-phenyl}-propionic acid

HRID 1929943Notes

Reaction equation

HRID 1929943 reaction equation
Br[C:2]1[C:3]([O:18][CH2:19][CH:20]2[CH2:22][CH2:21]2)=[N:4][CH:5]=[C:6]([CH:17]=1)[C:7]([NH:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[OH:16])=[O:8].[C:23]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)([O:25]CC)=[O:24]>>[CH:20]1([CH2:19][O:18][C:3]2[C:2]([C:33]3[CH:34]=[CH:35][C:30]([CH2:29][CH2:28][C:23]([OH:25])=[O:24])=[CH:31][CH:32]=3)=[CH:17][C:6]([C:7](=[O:8])[NH:9][C@@H:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]3[OH:16])=[CH:5][N:4]=2)[CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 38517004-(2-Ethoxycarbonylethyl)benzeneboronic acidHCID 675049715-bromo-6-cyclopropylmethoxy-N-(trans-2-hydroxy-cyclohexyl)-nicotinamide

Product 1

HCID 675054413-{4-[2-Cyclopropylmethoxy-5-((1R,2R)-2-hydroxy-cyclohexylcarbamoyl)-pyridin-3-yl]-phenyl}-propionic acid

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 31c, using 5-bromo-6-cyclopropylmethoxy-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide and 4-(2-carbethoxyethyl)benzene-boronic acid (commercially available) as starting materials to give the product as white solid, MS (ISP): 437.2 (M−H+).

Workup

  1. customdescribed for the preparation of Example 31c

Sources & evidence

ORD record
ord-023ff42cb6474edc9d15116c68753194
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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