1,1-dimethylethyl [2-({[2-(3-furanyl)-5-(1-methyl-1H-pyrazol-5-yl)-3-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate → N-[2-amino-1-(phenylmethyl)ethyl]-2-(3-furanyl)-5-(1-methyl-1H-pyrazol-5-yl)-3-thiophenecarboxamide

HRID 1967102Notes

Reaction equation

HRID 1967102 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[S:7][C:8]([C:31]3[N:35]([CH3:36])[N:34]=[CH:33][CH:32]=3)=[CH:9][C:10]=2[C:11]([NH:13][CH:14]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:15][NH:16]C(=O)OC(C)(C)C)=[O:12])=[CH:2]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:16][CH2:15][CH:14]([NH:13][C:11]([C:10]1[CH:9]=[C:8]([C:31]2[N:35]([CH3:36])[N:34]=[CH:33][CH:32]=2)[S:7][C:6]=1[C:3]1[CH:4]=[CH:5][O:1][CH:2]=1)=[O:12])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 1

HCID 581729091,1-dimethylethyl [2-({[2-(3-furanyl)-5-(1-methyl-1H-pyrazol-5-yl)-3-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate

Product 1

HCID 24997109N-[2-amino-1-(phenylmethyl)ethyl]-2-(3-furanyl)-5-(1-methyl-1H-pyrazol-5-yl)-3-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 1,1-dimethylethyl [2-({[2-(3-furanyl)-5-(1-methyl-1H-pyrazol-5-yl)-3-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate (crude from part e) in TFA-DCM (3 mL, 1:2) was stirred at 25° C. After 30 min, the solution was concentrated and the residue passed through a silica plug (3% MeOH in DCM (1% NH4OH)) affording the free base of the title compound.

Workup

  1. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-72c113f08e974e1d9ad2ba0e1f66b7d5
Source dataset
uspto-grants-2013_04
Patent number
US08420690B2

Reaction notes

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