Trifluoroacetic acid → HCID 67040834, compound

HRID 605056Notes

Reaction equation

HRID 605056 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([S: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]([S:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([Br:29])=[CH:27][CH:28]=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:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67040282HCID 67040282, compound

Product 1

HCID 67040834HCID 67040834, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 13D (106 mg, 0.1546 mmol) was treated with trifluoroacetic acid (3 mL) in methylene chloride (3 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 (50 mL), water, and brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Purification by silica gel flash chromatography with 5% methanol/methylene chloride provided the title compound as a light yellow solid (55 mg, 61%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.34 (d, J=6.99 Hz, 6 H) 3.13-3.31 (m, 1 H) 5.60 (s, 2 H) 6.63 (d, J=8.82 Hz, 2 H) 6.88 (d, J=8.46 Hz, 1 H) 7.14 (d, J=8.46 Hz, 2 H) 7.52 (d, J=8.82 Hz, 2 H) 7.64 (d, J=8.46 Hz, 1 H) 7.73 (d, J=8.82 Hz, 2 H) 7.78 (dd, J=8.27, 1.65 Hz, 1 H) 7.94 (d, J=1.47 Hz, 1 H) 8.59 (s, 1 H) 8.88 (d, J=8.82 Hz, 1 H) 10.16 (s, 1 H) 10.28 (s, 1 H); MS (ESI+) m/z 585/587 (M+H)+, MS (ESI−) m/z 583/585 (M−H)−.

Workup

  1. customThe solvents were removed by rotary evaporation
  2. washwashed with saturated aqueous sodium bicarbonate (50 mL), water, and brine
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel flash chromatography with 5% methanol/methylene chloride

Sources & evidence

ORD record
ord-f02dc7b4c3d1400fa689a504934cbd94
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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