Triethylamine → Trifluoroacetic acid

HRID 2236740Notes

Reaction equation

HRID 2236740 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]/OC.[CH3:17][N:18]1[CH2:22][CH2:21][CH:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[CH2:19]1.[C:31]([OH:37])([C:33]([F:36])([F:35])[F:34])=[O:32].C(N(CC)CC)C>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:30][C:27]1[CH:26]=[CH:25][C:24]([O:23][CH:20]2[CH2:21][CH2:22][N:18]([CH3:17])[CH2:19]2)=[CH:29][CH:28]=1.[C:31]([OH:37])([C:33]([F:36])([F:35])[F:34])=[O:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dioneHCID 86761110HCID 86761110, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 178480501HCID 178480501, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4E)-6-Bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (52 mg, 0.18 mmol) and 4-(1-methyl-pyrrolidin-3-yloxy)-phenylamine•TFA (55 mg, 0.18 mmol) were stirred in N,N-dimethylformamide (1 mL) and triethylamine (100 μL) at 75° C. The reaction mixture is purified by reverse phase high performance liquid chromatography to give (4Z)-6-bromo-4-[({4-[(1-methylpyrrolidin-3-yl)oxy]phenyl}amino)methylene]isoquinoline-1,3(2H,4H)-dione as its TFA salt.

Workup

  1. customat 75° C
  2. customThe reaction mixture is purified by reverse phase high performance liquid chromatography

Sources & evidence

ORD record
ord-41720dcb2ac64baaaa8b3cd21afc3e4f
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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