Trifluoroacetic acid → Trifluoroacetic acid

HRID 605145Notes

Reaction equation

HRID 605145 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([S: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]([CH:42]([CH3:44])[CH3:43])=[N:38][C:34]=3[N:35]=[CH:36][N:37]=2)[CH:9]=1)(C)(C)C.[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49]>ClCCl>[NH2:7][C:8]1[CH:9]=[C:10]([S:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=3)=[O:30])=[CH:17][C:16]=2[NH:31][C:32]2[C:33]3[CH:41]=[CH:40][C:39]([CH:42]([CH3:44])[CH3:43])=[N:38][C:34]=3[N:35]=[CH:36][N:37]=2)[CH:11]=[CH:12][CH:13]=1.[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67040184HCID 67040184, compound

Product 2

HCID 6422Trifluoroacetic acidYield 35%HCID 67040223HCID 67040223, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of the product of Example 95D (0.67 g, 0.98 mmol) in dichloromethane (10 mL) was added dropwise trifluoroacetic acid (5 mL). The solution was stirred for 30 minutes and concentrated under vacuum. The resultant residue was purified by HPLC with TFA to provide the title compound as a trifluoroacetic acid salt (15 mg, 35%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.36 (d, J=6.62 Hz, 6 H), 3.22-3.33 (m, 1 H), 6.31-6.64 (m, 3 H), 6.97 (t, J=7.91 Hz, 1 H), 7.23-7.41 (m, 3 H), 7.69-7.79 (m, 1 H), 7.83 (d, J=9.56 Hz, 1 H), 7.91 (d, J=11.03 Hz, 1 H Hz, 1 H), 7.99 (s, 1 H), 8.07 (s, 1 H), 8.79 (s, 1 H), 8.95 (d, J=7.35 Hz, 1 H), 10.41 (s, 1 H), 11.40 (s, 1 H).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe resultant residue was purified by HPLC with TFA

Sources & evidence

ORD record
ord-637da89982ba4b63b0e581c09c3eedda
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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