2-Methylpyridine-4-boronic acid → (1R,2R,4R)-2-Methoxy-4-[4-(2-methyl-pyridin-4-yl)-2-trifluoromethyl-benzenesulfonyl]-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide

HRID 1367534Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][C:2]=1[CH3:10].[C:11]([C:13]1([NH:16][C:17]([C@@H:19]2[CH2:23][C@@H:22]([S:24]([C:27]3[CH:32]=[CH:31][C:30](Br)=[CH:29][C:28]=3[C:34]([F:37])([F:36])[F:35])(=[O:26])=[O:25])[CH2:21][C@H:20]2[O:38][CH3:39])=[O:18])[CH2:15][CH2:14]1)#[N:12].C(C1(NC([C@H]2C[C@H](S(C3C=CC(Br)=CC=3C(F)(F)F)(=O)=O)C[C@@H]2OC)=O)CC1)#N>>[C:11]([C:13]1([NH:16][C:17]([C@@H:19]2[CH2:23][C@@H:22]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([C:4]4[CH:5]=[CH:6][N:1]=[C:2]([CH3:10])[CH:3]=4)=[CH:29][C:28]=3[C:34]([F:35])([F:36])[F:37])(=[O:25])=[O:26])[CH2:21][C@H:20]2[O:38][CH3:39])=[O:18])[CH2:14][CH2:15]1)#[N:12]

Participants

Reactant 3

HCID 41926642-Methylpyridine-4-boronic acid

HCID 59619295(1R,2R,4R)-4-(4-bromo-2-trifluoromethyl-benzenesulfonyl)-2-methoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide

HCID 59619475(1S,2S,4S)-4-(4-Bromo-2-trifluoromethyl-benzenesulfonyl)-2-methoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide

Product 1

HCID 59619258(1R,2R,4R)-2-Methoxy-4-[4-(2-methyl-pyridin-4-yl)-2-trifluoromethyl-benzenesulfonyl]-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide

Procedure

The title compound was prepared in analogy to example 62 using 2-picoline-4-boronic acid instead of 2.4-difluorophenylboronic acid and (1R,2R,4R)-4-(4-bromo-2-trifluoromethyl-benzenesulfonyl)-2-methoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide (example 137) instead of (1R,2R,4R) and (1S,2S,4S)-4-(4-bromo-2-trifluoromethyl-benzenesulfonyl)-2-methoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide. Pink solid. MS (EI): 508.1 (M+H)+.

Sources & evidence

ORD record: ord-09f47698cf094ec99bda47ac38eee62e
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893099B2

Reaction notes

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