HCID 86633548, compound → HCID 24993442, compound

HRID 1961010Notes

Reaction equation

HRID 1961010 reaction equation
CC([N:5]([CH2:9][CH:10]([NH:18][C:19]([C:21]1[S:22][C:23]([C:29]2[N:33]([CH3:34])[N:32]=[CH:31][CH:30]=2)=[C:24]([Br:28])[C:25]=1[O:26][CH3:27])=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C(=O)[O-])(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:5][CH2:9][CH:10]([NH:18][C:19]([C:21]1[S:22][C:23]([C:29]2[N:33]([CH3:34])[N:32]=[CH:31][CH:30]=2)=[C:24]([Br:28])[C:25]=1[O:26][CH3:27])=[O:20])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 1

HCID 86633548HCID 86633548, compound

Product 1

HCID 24993442HCID 24993442, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 1,1-dimethylethyl[2-({[4-bromo-3-(methyloxy)-5-(1-methyl-1H-pyrazol-5-yl)-2-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 neutralized 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-b25aa54f6a294b069a241cc7aa0f666d
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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