Trifluoroacetic acid → Trifluoroacetic acid

HRID 605155Notes

Reaction equation

HRID 605155 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=3)=[CH:17][C:16]=2[NH:31][C:32]2[C:33]3[CH:41]=[CH:40][C:39]([CH3:42])=[N:38][C:34]=3[N:35]=[CH:36][N:37]=2)[CH:9]=1)(C)(C)C.[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47]>>[NH2:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=2)=[O:30])=[CH:17][C:16]=1[NH:31][C:32]1[C:33]2[CH:41]=[CH:40][C:39]([CH3:42])=[N:38][C:34]=2[N:35]=[CH:36][N:37]=1.[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67040342HCID 67040342, compound

Product 2

HCID 6422Trifluoroacetic acidYield 87%HCID 67040387HCID 67040387, compound

Procedure

The product of Example 108 (0.028 g, 0.044 mmol) was treated with trifluoroacetic acid as in the procedure for Example 96. The crude product was purified by trituration in dichloromethane to give the title compound as a trifluoroacetic acid salt (0.025 g, 87%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 2.75 (s, 3 H), 6.24 (d, J=8.09 Hz, 1 H), 6.30 (s, 1 H), 6.39 (d, J=7.72 Hz, 1 H), 7.01 (t, J=7.91 Hz, 1 H), 7.12 (d, J=8.82 Hz, 1 H), 7.25-7.40 (m, 2 H), 7.69-7.78 (m, 1 H, 7.82 (d, J=8.82 Hz, 1 H), 8.03 (dd, J=8.64, 2.39 Hz, 1 H), 8.12 (dd, J=17.46, 2.02 Hz, 2 H), 8.88-9.00 (m, 2 H), 10.41 (s, 1 H), 11.60 (s, 1 H); MS (ESI+) m/z 541/543 (M+H)+.

Workup

  1. customThe crude product was purified by trituration in dichloromethane

Sources & evidence

ORD record
ord-d1e373dd4f674162bc8f1f0867886d73
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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