Trifluoroacetic acid → HCID 24757709, compound

HRID 605052Notes

Reaction equation

HRID 605052 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]([Br: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.FC(F)(F)C(O)=O>C(Cl)Cl>[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]([Br: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

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67040643HCID 67040643, compound

Product 1

HCID 24757709HCID 24757709, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 10D (2.78 g, 4.152 mmol) was treated with trifluoroacetic acid (25 mL) in methylene chloride (25 mL) at room temperature for 30 minutes. The solvents were removed under vacuum by rotary evaporation and the residual oil taken up in ethyl acetate (400 mL) and washed with saturated aqueous sodium bicarbonate (2×100 mL), water (2×100 mL), and brine (100 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting solid was triturated with 3% methanol/methylene chloride and dried in vacuo to afford the title compound as a light beige solid (1.77 g, 75%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.32 (d, J=6.99 Hz, 6 H) 3.09-3.31 (m, 1 H) 5.03 (s, 2 H) 6.57 (d, J=8.82 Hz, 2 H) 6.78 (d, J=8.82 Hz, 2 H) 6.83 (d, J=8.82 Hz, 1 H) 7.53 (d, J=8.82 Hz, 2 H) 7.60 (d, J=8.82 Hz, 1 H) 7.75 (d, J=9.19 Hz, 2 H) 7.85 (dd, J=8.46, 2.21 Hz, 1 H) 8.16 (d, J=2.21 Hz, 1 H) 8.62 (s, 1 H) 8.84 (d, J=8.46 Hz, 1 H) 10.00 (s, 1 H) 10.29 (s, 1 H); MS (ESI+) m/z 569/571 (M+H)+, MS (ESI−) m/z 567/569 (M−H)−.

Workup

  1. customThe solvents were removed under vacuum by rotary evaporation
  2. washwashed with saturated aqueous sodium bicarbonate (2×100 mL), water (2×100 mL), and brine (100 mL)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid was triturated with 3% methanol/methylene chloride
  7. customdried in vacuo

Sources & evidence

ORD record
ord-423fd575809b4efea810bee1569cd06c
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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