4-Chlorophenylboronic acid → HCID 11952381, compound

HRID 1766493Notes

Reaction equation

HRID 1766493 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([OH:11])=O)[CH:5]=[N:6][C:7]=1Cl.[OH:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH2:19])=[O:18].[Cl:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.Cl.[NH2:31][C@@H:32]1[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]1[OH:38]>>[C:17]([CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:7]1[C:2]([C:24]2[CH:25]=[CH:26][C:21]([Cl:20])=[CH:22][CH:23]=2)=[CH:3][C:4]([C:9]([NH:31][C@@H:32]2[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]2[OH:38])=[O:11])=[CH:5][N:6]=1)(=[O:18])[NH2:19]

Participants

5

Reactant 4

HCID 742994-Chlorophenylboronic acidHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 329061Pentanamide, 5-hydroxy-HCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-

Product 1

HCID 11952381HCID 11952381, compound

Procedure

The title compound was synthesized in analogy to Example 75, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, 5-hydroxyvaleramide, (4-chloro-phenyl)-boronic acid and (1R,2R)-2-amino-cyclohexanol hydrochloride as starting materials to yield 6-(4-carbamoyl-butoxy)-5-(4-chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide. MS (ISP) 446.1 (M+H)+.

Workup

  1. customThe title compound was synthesized in analogy to Example 75

Sources & evidence

ORD record
ord-283abccaf01f45c8b0e575fc2c0fcf2e
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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