Trifluoroacetic acid → Trifluoroacetic acid

HRID 607256Notes

Reaction equation

HRID 607256 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([S:21](=[O:31])(=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=3)=[CH:17][C:16]=2[NH:32][C:33]2[C:34]3[CH:42]=[CH:41][C:40]([CH:43]([CH3:45])[CH3:44])=[N:39][C:35]=3[N:36]=[CH:37][N:38]=2)=[CH:10][CH:9]=1)(C)(C)C.[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50]>C(Cl)Cl>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=3)(=[O:30])=[O:31])=[CH:17][C:16]=2[NH:32][C:33]2[C:34]3[CH:42]=[CH:41][C:40]([CH:43]([CH3:45])[CH3:44])=[N:39][C:35]=3[N:36]=[CH:37][N:38]=2)=[CH:10][CH:9]=1.[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66808685HCID 66808685, compound

Product 2

HCID 6422Trifluoroacetic acidYield 48%HCID 60204800HCID 60204800, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 149E (44 mg, 0.061 mmol) was treated with trifluoroacetic acid (2 mL) in methylene chloride (2 mL) at room temperature for 30 minutes. The solvents were removed by rotary evaporation under vacuum and the residual oil dried under hi-vacuum. Purification by silica gel chromatography using 5% methanol/methylene chloride as eluent provided the title compound as a trifluoroacetic acid salt (25 mg, 48%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.35 (d, J=6.62 Hz, 6H), 3.13-3.38 (m, 1H), 6.63 (d, J=8.46 Hz, 2H), 6.87 (d, J=7.72 Hz, 1H), 7.01-7.09 (d, J=8.82 Hz, 2H), 7.12 (d, J=8.46 Hz, 2H), 7.44 (d, J=8.82 Hz, 2H), 7.61 (dd, J=7.72, 1.47 Hz, 1H), 7.71 (s, 1H), 7.81 (dd, J=6.62, 1.47 Hz, 1H), 8.66-8.80 (m, 1H), 8.90 (d, J=6.99 Hz, 1H), 10.55 (s, 1H); MS (ESI+) m/z 621/623 (M+H)+.

Workup

  1. customThe solvents were removed by rotary evaporation under vacuum
  2. customthe residual oil dried under hi-vacuum
  3. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-9b898743b291438a9231792f9644f3a3
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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