Trifluoroacetic acid → HCID 67040955, compound

HRID 605215Notes

Reaction equation

HRID 605215 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]([Cl:29])=[CH:25][N: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]([Cl:29])=[CH:25][N: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 67040281HCID 67040281, compound

Product 1

HCID 67040955HCID 67040955, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 199D (162.2 g, 0.2591 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 and the residual oil taken up in ethyl acetate (75 mL) and washed with saturated aqueous sodium bicarbonate (30 mL), water (2×30 mL), and brine (30 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Purification by silica gel chromatography eluting with 4% methanol/methylene chloride afforded the title compound (104 mg, 76%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.32 (d, J=6.99 Hz, 6 H) 3.09-3.30 (m, 1 H) 5.04 (s, 2 H) 6.57 (d, J=8.82 Hz, 2 H) 6.78 (d, J=8.83 Hz, 1 H) 6.79 (d, J=8.82 Hz, 2 H) 7.60 (d, J=8.46 Hz, 1 H) 7.94-7.98 (m, 2 H) 8.20-8.27 (m, 2 H) 8.43 (d, J=2.94 Hz, 1 H) 8.62 (s, 1 H) 8.85 (d, J=8.46 Hz, 1 H) 9.97 (s, 1 H) 10.91 (s, 1 H); MS (ESI+) m/z 526/528 (M+H)+.

Workup

  1. customThe solvents were removed by rotary evaporation
  2. washwashed with saturated aqueous sodium bicarbonate (30 mL), water (2×30 mL), and brine (30 mL)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography
  7. washeluting with 4% methanol/methylene chloride

Sources & evidence

ORD record
ord-513a7e93f25c453ea14a949e314185da
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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