Trifluoroacetic acid → Trifluoroacetic acid

HRID 883978Notes

Reaction equation

HRID 883978 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 78E (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, 6 H), 3.13-3.38 (m, 1 H), 6.63 (d, J=8.46 Hz, 2 H), 6.87 (d, J=7.72 Hz, 1 H), 7.01-7.09 (d, J=8.82 Hz, 2 H), 7.12 (d, J=8.46 Hz, 2 H), 7.44 (d, J=8.82 Hz, 2 H), 7.61 (dd, J=7.72, 1.47 Hz, 1 H), 7.71 (s, 1 H), 7.81 (dd, J=6.62, 1.47 Hz, 1 H), 8.66-8.80 (m, 1 H), 8.90 (d, J=6.99 Hz, 1 H), 10.55 (s, 1 H); 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-67e6fad0331f419f8f7639d6436d0481
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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