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

HRID 1929883Notes

Reaction equation

HRID 1929883 reaction equation
Br[C:2]1C(OCC2CC2)=NC=C(C=1)C(O)=O.[C:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)#[N:17].[CH:27]1([CH2:30][O:31][C:32]2[C:47](C3C=CC(F)=C(F)C=3)=[CH:46][C:35]([C:36]([NH:38][C@@H:39]3C[CH2:43][CH2:42][CH2:41][C@H:40]3[OH:45])=[O:37])=[CH:34][N:33]=2)[CH2:29][CH2:28]1>>[C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:47]2[C:32]([O:31][CH2:30][CH:27]3[CH2:28][CH2:29]3)=[N:33][CH:34]=[C:35]([CH:46]=2)[C:36]([NH:38][CH2:39][C@@:40]([CH:41]2[CH2:42][CH2:43]2)([OH:45])[CH3:2])=[O:37])=[CH:20][CH:19]=1)#[N:17]

Participants

4

Reactant 3

HCID 27343264-Cyanophenylboronic acidHCID 119514806-Cyclopropylmethoxy-5-(3,4-difluoro-phenyl)-N-((trans)-2-hydroxy-cyclohexyl)-nicotinamideHCID 211097085-Bromo-6-(cyclopropylmethoxy)nicotinic acid

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 31 b), to give the title compound as a white solid, MS (ISP): 392.2 (M+H)+.

Sources & evidence

ORD record
ord-471f98baba19483e8e27ed2bfad5df5d
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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