3,5-Dimethylisoxazole-4-boronic acid → (1S,2S,4S)-4-[4-(3,5-Dimethyl-isoxazol-4-yl)-2-trifluoromethyl-benzenesulfonyl]-2-isopropoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide

HRID 1367536Notes

Reaction equation

HRID 1367536 reaction equation
[CH3:1][C:2]1[C:6](B(O)O)=[C:5]([CH3:10])[O:4][N:3]=1.[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][CH:39]([CH3:41])[CH3:40])=[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:6]4[C:2]([CH3:1])=[N:3][O:4][C:5]=4[CH3:10])=[CH:29][C:28]=3[C:34]([F:37])([F:35])[F:36])(=[O:26])=[O:25])[CH2:21][C@@H:20]2[O:38][CH:39]([CH3:41])[CH3:40])=[O:18])[CH2:15][CH2:14]1)#[N:12]

Participants

4

Reactant 3

HCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 59619427(1S,2S,4S)-4-(4-bromo-2-trifluoromethyl-benzenesulfonyl)-2-isopropoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amideHCID 59619475(1S,2S,4S)-4-(4-Bromo-2-trifluoromethyl-benzenesulfonyl)-2-methoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide

Product 1

HCID 59619448(1S,2S,4S)-4-[4-(3,5-Dimethyl-isoxazol-4-yl)-2-trifluoromethyl-benzenesulfonyl]-2-isopropoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide

Procedure

The title compound was prepared in analogy to example 62 using 3,5-dimethyl-isoxazole-4-boronic acid instead of 2.4-difluorophenylboronic acid and (1R,2R,4R) and (1S,2S,4S)-4-(4-bromo-2-trifluoromethyl-benzenesulfonyl)-2-isopropoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide instead of (1R,2R,4R) and (1S,2S,4S)-4-(4-bromo-2-trifluoromethyl-benzenesulfonyl)-2-methoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide. White solid. MS (EI): 538.2 (M−H)−.

Sources & evidence

ORD record
ord-1ffeaae040514307baa18badd01106ef
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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