Trifluoroacetic acid → HCID 118275227, compound

HRID 526018Notes

Reaction equation

HRID 526018 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][C:9]([C:11](=[O:28])[NH:12][CH:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[C:14]([F:17])([F:16])[F:15])=[CH:10][C:5]2=[CH:4][C:3]=1[CH2:29][NH:30]C(=O)OC(C)(C)C.F[C:39](F)(F)[C:40](O)=O>ClCCl>[NH2:30][CH2:29][C:3]1[CH:4]=[C:5]2[CH:10]=[C:9]([C:11]([NH:12][CH:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[C:14]([F:17])([F:15])[F:16])=[O:28])[N:8]([CH2:39][CH3:40])[C:6]2=[N:7][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735593HCID 131735593, compound

Product 1

HCID 118275227HCID 118275227, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl {[6-methyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methyl}carbamate (274 mg, 0.46 mmol) was initially charged in dichloromethane (5.0 ml), trifluoroacetic acid (526 mg, 4.61 mmol) was added and the mixture was stirred at room temperature for 2 hours. The solvent was removed completely under reduced pressure, giving 210 mg (86% of theory) of 5-(aminomethyl)-1-ethyl-6-methyl-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-pyrrolo[2,3-b]pyridine-2-carboxamide, which were directly reacted further. HPLC-MS: log P=1.94; mass (m/z): 460.1.

Workup

  1. customThe solvent was removed completely under reduced pressure

Sources & evidence

ORD record
ord-470f5e3b6f2f4af88883dc7891ef9143
Source dataset
uspto-grants-2016_05
Patent number
US09345247B2

Reaction notes

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