Trifluoroacetic acid → Trifluoroacetic acid

HRID 605128Notes

Reaction equation

HRID 605128 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][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:10][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:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][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]([CH3:43])[CH3:44])=[N:38][C:34]=3[N:35]=[CH:36][N:37]=2)=[CH:10][CH:9]=1.[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67040245HCID 67040245, compound

Product 2

HCID 6422Trifluoroacetic acidYield 14%HCID 67040112HCID 67040112, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 86E (305 mg, 0.504 mmol) was dissolved in dichloromethane (5 mL) and trifluoroacetic acid (2 mL). The solution was stirred at room temperature for 1 hour at which time the solvent was removed on the under vacuum. The resultant residue was purified by HPLC with TFA to provide the title compound as a trifluoroacetic acid salt (35 mg, 14%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.34 (d, J=6.99 Hz, 6 H), 2.28 (s, 3 H), 3.28 (qt, J=13.70, 6.94 Hz, 1 H), 6.82-6.88 (m, 2 H), 6.91-6.99 (m, 3 H), 7.16 (d, J=8.46 Hz, 2 H), 7.63 (d, J=8.46 Hz, 2 H), 7.86 (d, J=8.46 Hz, 1 H), 7.98 (dd, J=8.46, 2.21 Hz, 1 H), 8.13 (d, J=2.21 Hz, 1 H), 8.87 (s, 1 H), 8.98 (d, J=8.46 Hz, 1 H), 10.17 (s, 1 H); MS (ESI+) m/z 505 (M+H-TFA)+; (ESI−) m/z 503 (M−H-TFA)−.

Workup

  1. customwas removed on the under vacuum
  2. customThe resultant residue was purified by HPLC with TFA

Sources & evidence

ORD record
ord-4f4b3723ae7c495bb2b49b4d50a4c1f1
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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