Trifluoroacetic acid → N-(4,4-Dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-2-(4-fluoro-benzylamino)-benzamide

HRID 969674Notes

Reaction equation

HRID 969674 reaction equation
C(OC([N:8]1[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]2[C:10](=[CH:11][C:12]([NH:20][C:21](=[O:37])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[NH:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:18][C:16]1([CH3:19])[C:15]2[C:10](=[CH:11][C:12]([NH:20][C:21](=[O:37])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[NH:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)=[CH:13][CH:14]=2)[CH2:9][NH:8][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 695108657-[2-(4-Fluoro-benzylamino)-benzoylamino]-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 1

HCID 59017467N-(4,4-Dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-2-(4-fluoro-benzylamino)-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-[2-(4-Fluoro-benzylamino)-benzoylamino]-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (Step B, 0.57 g, 1.13 mmol) was treated with 10 mL of 50% of TFA in CH2Cl2 and stirred at RT for 1 h. The volatiles were removed under reduced pressure, and the residue was purified by flash column chromatography. The titled compound was obtained as a white solid. MS (ES+): 404 (M+H)+. Calc'd for C25H26FN3O-403.21.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-1d82d8995bfe4d9fa30c580102f1f6a9
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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