4-Acetamidophenylboronic acid → N1-[(1R)-1-[4'-(acetylamino)-4-biphenylyl]-2-(1-pyrrolidinyl)ethyl]-N2-(cyanomethyl)-N2-(3,4-dichlorophenyl)-N1-methylglycinamide

HRID 2354425Notes

Reaction equation

HRID 2354425 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:15][CH3:16])[CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[C:17]([CH2:19][N:20]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=1)[CH2:21][C:22]([OH:24])=O)#[N:18].[C:33]([NH:36][C:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1)(=[O:35])[CH3:34]>>[C:33]([NH:36][C:37]1[CH:42]=[CH:41][C:40]([C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]([N:15]([CH3:16])[C:22](=[O:24])[CH2:21][N:20]([CH2:19][C:17]#[N:18])[C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=3)[CH2:9][N:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:4][CH:3]=2)=[CH:39][CH:38]=1)(=[O:35])[CH3:34]

Participants

4

Reactant 3

HCID 27346574-Acetamidophenylboronic acidHCID 57418651HCID 57418651, compoundHCID 57501277[(1R)-1-(4-bromophenyl)-2-(1-pyrrolidinyl)ethyl]methylamine

Product 1

HCID 59809643N1-[(1R)-1-[4'-(acetylamino)-4-biphenylyl]-2-(1-pyrrolidinyl)ethyl]-N2-(cyanomethyl)-N2-(3,4-dichlorophenyl)-N1-methylglycinamide

Procedure

Proceeding in a similar manner as in example 85, but replacing 1-(4-bromophenyl)-N-methyl-2-(1-pyrrolidinyl)ethanamine with (1R)-1-(4-bromophenyl)-N-methyl-2-(1-pyrrolidinyl)ethanamine and replacing (6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)acetic acid with N-(cyanomethyl)-N-(3,4-dichlorophenyl)glycine in step a) and replacing 3,4-dimethoxyphenylboronic acid with [4-(acetylamino) phenyl]boronic acid in step b), the title compound was prepared. MS (ES) m/e 578 [M+H]+.

Sources & evidence

ORD record
ord-4b34d3361e32457489db7fa194f3e886
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

Loading…