4-Chlorophenylboronic acid → 5-(4-chloro-phenyl)-N-((R)-2-cyclopropyl-2-hydroxy-propyl)-6-cyclopropylmethoxy-nicotinamide

HRID 1159280Notes

Reaction equation

HRID 1159280 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([OH:11])=O)[CH:5]=[N:6][C:7]=1Cl.[CH:12]1([CH2:15][OH:16])[CH2:14][CH2:13]1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.[NH2:27][CH2:28][C@@:29]([CH3:34])([CH:31]1[CH2:33][CH2:32]1)[OH:30]>>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[C:7]([O:16][CH2:15][CH:12]3[CH2:14][CH2:13]3)=[N:6][CH:5]=[C:4]([CH:3]=2)[C:9]([NH:27][CH2:28][C@@:29]([CH:31]2[CH2:33][CH2:32]2)([OH:30])[CH3:34])=[O:11])=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 742994-Chlorophenylboronic acidHCID 75644CyclopropanemethanolHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 51684102(2R)-1-amino-2-cyclopropyl-propan-2-ol

Product 1

HCID 248565545-(4-chloro-phenyl)-N-((R)-2-cyclopropyl-2-hydroxy-propyl)-6-cyclopropylmethoxy-nicotinamide

Procedure

The title compound was synthesized in analogy to Example 31, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, cyclopropanemethanol, (4-chloro-phenyl)-boronic acid and (R)-α-(aminomethyl)-α-methyl-cyclopropanemethanol as starting materials to yield 5-(4-chloro-phenyl)-N—((R)-2-cyclopropyl-2-hydroxy-propyl)-6-cyclopropylmethoxy-nicotinamide as a white solid, MS (ISP) 401.3 (M+H)+.

Workup

  1. customThe title compound was synthesized in analogy to Example 31

Sources & evidence

ORD record
ord-39a6f4d404c441449790d45c9bdcd02b
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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