4-Aminophenylboronic acid → (S,S)-(1-{2-[2-(4-amino-phenyl)-imidazo[2,1-b]thiazol-6-ylcarbamoyl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

HRID 716517Notes

Reaction equation

HRID 716517 reaction equation
[CH3:1][O:2][C:3](=[O:28])[NH:4][C@H:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:27])[NH:17][C:18]1[N:19]=[C:20]2[N:24]([CH:25]=1)[CH:23]=[C:22](Br)[S:21]2)=[O:10])[CH:6]([CH3:8])[CH3:7].[NH2:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1>>[CH3:1][O:2][C:3](=[O:28])[NH:4][C@H:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:27])[NH:17][C:18]1[N:19]=[C:20]2[N:24]([CH:25]=1)[CH:23]=[C:22]([C:33]1[CH:34]=[CH:35][C:30]([NH2:29])=[CH:31][CH:32]=1)[S:21]2)=[O:10])[CH:6]([CH3:8])[CH3:7]

Participants

3

Reactant 2

HCID 27346154-Aminophenylboronic acidHCID 67241387(S,S)-{1-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester

Product 1

HCID 53304097(S,S)-(1-{2-[2-(4-amino-phenyl)-imidazo[2,1-b]thiazol-6-ylcarbamoyl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

Procedure

Compound A25 was synthesized from 12b (0.318 mmol) and 4-aminophenylboronic acid (0.477 mmol), following the procedure as described for compound A1, to give compound A25 as a white solid in 29%. MS (ESI, EI+) m/z=485.15 (MH+).

Workup

  1. customto give compound A25 as a white solid in 29%

Sources & evidence

ORD record
ord-3982d0775a584b5cb176c267702b960d
Source dataset
uspto-grants-2015_11
Patent number
US09187496B2

Reaction notes

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