4-{4-[2-[1-(2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-yl]-phenyl]-piperazine-1-carboxylic acid benzyl ester → (2-methyl-1-{2-[5-(4-piperazin-1-yl-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-propyl)-carbamic acid methyl ester

HRID 71785Notes

Reaction equation

HRID 71785 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[N:24]([CH2:44][O:45][CH2:46][CH2:47][Si:48]([CH3:51])([CH3:50])[CH3:49])[C:25]([CH:28]4[CH2:32][CH2:31][CH2:30][N:29]4[C:33](=[O:43])[CH:34]([NH:38][C:39]([O:41][CH3:42])=[O:40])[CH:35]([CH3:37])[CH3:36])=[N:26][CH:27]=3)=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CCO>[CH3:42][O:41][C:39](=[O:40])[NH:38][CH:34]([C:33]([N:29]1[CH2:30][CH2:31][CH2:32][CH:28]1[C:25]1[N:24]([CH2:44][O:45][CH2:46][CH2:47][Si:48]([CH3:50])([CH3:51])[CH3:49])[C:23]([C:20]2[CH:21]=[CH:22][C:17]([N:14]3[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]3)=[CH:18][CH:19]=2)=[CH:27][N:26]=1)=[O:43])[CH:35]([CH3:37])[CH3:36]

Participants

3

Reactant 1

HCID 666202604-{4-[2-[1-(2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-yl]-phenyl]-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 66620632(2-methyl-1-{2-[5-(4-piperazin-1-yl-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-propyl)-carbamic acid methyl esterYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-{4-[2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-yl]-phenyl}-piperazine-1-carboxylic acid benzyl ester (166 mg, 0.23 mmol) in EtOH (2.5 mL) was treated with 20% PdOH/C (60 mg) and placed under an atmosphere of H2. The reaction was stirred for 18 hours and filtered through a CELITE plug to afford crude (2-methyl-1-{2-[5-(4-piperazin-1-yl-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-propyl)-carbamic acid methyl ester (120 mg), which was used without further purification: MS (ESI) m/z 585 [M+H]+.

Workup

  1. filtrationfiltered through a CELITE plug

Sources & evidence

ORD record
ord-4eee91477b2a4a04959aa3b1576a908f
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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