4-(Methanesulfonyl)phenylboronic acid → (2S)-2-{(S)-[(4'-methanesulfonylbiphenyl-4-yl)-thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid (1-cyanocyclopropyl)-amide
Reaction equation
[C:1]([C:3]1([NH:6][C:7](=[O:34])[C@@H:8]([NH:13][C@@H:14]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29](F)=[CH:28][C:27]=3F)=[CH:22][CH:21]=2)[C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:5][CH2:4]1)#[N:2].C(C1(NC(=O)[C@@H](N[C@@H](C2C=CC(Br)=CC=2)C2SC=CN=2)CC(C)C)CC1)#N.[CH3:62][S:63](C1C=CC(B(O)O)=CC=1)(=[O:65])=[O:64]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([C:3]1([NH:6][C:7](=[O:34])[C@@H:8]([NH:13][C@@H:14]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([S:63]([CH3:62])(=[O:65])=[O:64])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:5][CH2:4]1)#[N:2]Participants
5
Reactant 3
HCID 27343644-(Methanesulfonyl)phenylboronic acid
HCID 59715509(2S)-2-{(S)-[(2', 4'-difluorobiphenyl-4-yl)-thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid (1-cyanocyclopropyl)-amide
HCID 67298346(2S)2-{(S)-[(4-bromophenyl)-thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid (1-cyanocyclopropyl)-amideProduct 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared in similar manner to that described for (2S)-2-{(S)-[(2′,4′-difluorobiphenyl-4-yl)-thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid (1-cyanocyclopropyl)-amide, via Suzuki cross-coupling of (2S)-2-{(S)-[(4-bromophenyl)-thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid (1-cyanocyclopropyl)-amide with 4-methanesulfonylphenylboronic acid, in the presence of [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II), dichloromethane complex.
Sources & evidence
- ORD record
- ord-a61dd3ad52dc4cc8a2ab22d00b42d707
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07375134B2
Reaction notes
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