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

HRID 1159279Notes

Reaction equation

HRID 1159279 reaction equation
Br[C:2]1[C:3]([O:11][CH2:12][CH:13]2[CH2:15][CH2:14]2)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[C:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)#[N:17].[NH2:27][CH2:28][C@@:29]([CH3:34])([CH:31]1[CH2:33][CH2:32]1)[OH:30]>>[C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:2]2[C:3]([O:11][CH2:12][CH:13]3[CH2:15][CH2:14]3)=[N:4][CH:5]=[C:6]([CH:10]=2)[C:7]([NH:27][CH2:28][C@@:29]([CH:31]2[CH2:33][CH2:32]2)([OH:30])[CH3:34])=[O:9])=[CH:20][CH:19]=1)#[N:17]

Participants

4

Reactant 3

HCID 27343264-Cyanophenylboronic acidHCID 211097085-Bromo-6-(cyclopropylmethoxy)nicotinic acidHCID 51684102(2R)-1-amino-2-cyclopropyl-propan-2-ol

Product 1

HCID 675051495-(4-Cyano-phenyl)-N-((R)-2-cyclopropyl-2-hydroxy-propyl)-6-cyclopropylmethoxy-nicotinamide

Procedure

The title compound was synthesized from 5-bromo-6-cyclopropylmethoxy-nicotinic acid (example 31 a) by Suzuki reaction with 4-cyanophenyl-boronic acid (in analogy to 31 c) and amide coupling with (R)-α-(aminomethyl)-α-methyl-cyclopropanemethanol (WO 2006/106054) (in analogy to example 31b), to give the title compound as a white solid, MS (ISP): 392.2 (M+H)+.

Sources & evidence

ORD record
ord-79755774c9a647b3860dd79c82e1ff3b
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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