Trifluoroacetic acid → N-Methyl-3-(methyloxy)-4-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yloxy)benzamide

HRID 641550Notes

Reaction equation

HRID 641550 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:29]=[CH:28][C:15]3[CH2:16][CH2:17][N:18](C(OC(C)(C)C)=O)[CH2:19][CH2:20][C:14]=3[CH:13]=2)=[C:7]([O:30][CH3:31])[CH:6]=1)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:1][NH:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:29]=[CH:28][C:15]3[CH2:16][CH2:17][NH:18][CH2:19][CH2:20][C:14]=3[CH:13]=2)=[C:7]([O:30][CH3:31])[CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 574402991,1-Dimethylethyl 7-{[4-[(methylamino)carbonyl]-2-(methyloxy)phenyl]oxy}-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 57440300N-Methyl-3-(methyloxy)-4-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yloxy)benzamideYield 103.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 7-{[4-[(methylamino)carbonyl]-2-(methyloxy)phenyl]oxy}-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (E264, Step 5) (100 mg, 0.23 mmol) was dissolved in dry dichloromethane (2 ml), treated with trifluoroacetic acid (1 ml) and the resulting mixture was stirred at room temperature for 2 hours. The solvent was removed in vacuo and the residue dissolved in methanol and applied to a SCX column eluting with methanol and then a mixture of 0.880 ammonia:methanol (1:9). The basic fractions were combined and concentrated in vacuo to afford the title compound (78 mg); MS (ES+) m/e 327 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in methanol
  3. washeluting with methanol
  4. additiona mixture of 0.880 ammonia:methanol (1:9)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7fc60024d4f54ad6953d8e17e78bc23e
Source dataset
uspto-grants-2010_04
Patent number
US07696193B2

Reaction notes

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