Trifluoroacetic acid methylene chloride → HCID 59684239, compound

HRID 602276Notes

Reaction equation

HRID 602276 reaction equation
[C:1]([NH:5][C:6](=[O:38])[CH2:7][N:8]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([O:25][CH3:26])[CH:19]=2)=[CH:16][C:15]2[C:10](=[CH:11][C:12]([O:27]CC3C=CC(OC)=CC=3)=[CH:13][CH:14]=2)[C:9]1=[O:37])([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O.C(Cl)Cl>>[C:1]([NH:5][C:6](=[O:38])[CH2:7][N:8]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([O:25][CH3:26])[CH:19]=2)=[CH:16][C:15]2[C:10](=[CH:11][C:12]([OH:27])=[CH:13][CH:14]=2)[C:9]1=[O:37])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 59684236HCID 59684236, compound

Product 1

HCID 59684239HCID 59684239, compoundYield 27.3%

Procedure

N-tert-Butyl-2-(3-(4-fluoro-3-methoxyphenyl)-7-(4-methoxybenzyloxy)-1-oxo-1H-isoquinolin-2-yl)acetamide (120 mg, 0.231 mmol) was treated with TFA:DCM (1:1 v/v, 5 mL) and stirred at room temperature for 1 h. The mixture was concentrated in vacuo and the crude residue was purified by preparative HPLC giving N-tert-butyl-2-(3-(4-fluoro-3-methoxyphenyl)-7-hydroxy-1-oxo-1H-isoquinolin-2-yl)acetamide (INTERMEDIATE III.1) (25 mg, 0.063 mmol, 27%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-4d3310899c52456eb1cddf36360e4a39
Source dataset
uspto-grants-2011_03
Patent number
US07906504B2

Reaction notes

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