Acetyl chloride → HCID 72721200, compound

HRID 626986Notes

Reaction equation

HRID 626986 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(N(CC)CC)C.[F:12][CH:13]([F:43])[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][C:22]1[N:26]2[CH:27]=[C:28]([C:32]3[CH:37]=[CH:36][C:35]([S:38]([NH2:41])(=[O:40])=[O:39])=[CH:34][CH:33]=3)[C:29]([CH3:31])=[CH:30][C:25]2=[N:24][C:23]=1[CH3:42]>C(Cl)Cl>[F:43][CH:13]([F:12])[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][C:22]1[N:26]2[CH:27]=[C:28]([C:32]3[CH:37]=[CH:36][C:35]([S:38]([NH:41][C:1](=[O:3])[CH3:2])(=[O:39])=[O:40])=[CH:34][CH:33]=3)[C:29]([CH3:31])=[CH:30][C:25]2=[N:24][C:23]=1[CH3:42]

Participants

5

Reactant 3

HCID 6367Acetyl chloride3×HCID 8471Triethylamine3×HCID 72721106HCID 72721106, compound

Product 1

HCID 72721200HCID 72721200, compoundYield 14.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (24 μL, 0.34 mmol) and triethylamine (47 μL, 0.34 mmol) were added to a solution of Example 78 (154 mg, 0.34 mmol) in DCM (3 mL). The reaction mixture was stirred at room temperature for 2.5 h. Further acetyl chloride (12 μL, 0.17 mmol) and triethylamine (23 μL, 0.17 mmol) were added, and the mixture was stirred at room temperature for 24 h. Further acetyl chloride (49 μL, 0.68 mmol) and triethylamine (94 μL, 0.34 mmol) were added, and the mixture was stirred for 3 days. The solvent was removed and the mixture was purified by silica gel chromatography, eluting with a 0-5% gradient of 7M ammonia/methanol in DCM, to afford the title compound (24.8 mg, 14%) as a white solid. δH (250 MHz, CDCl3) 8.09 (d, J 8.4 Hz, 2H), 7.64 (d, J 19.1 Hz, 2H), 7.42 (s, 1H), 7.35 (d, J 8.3 Hz, 2H), 7.26 (m, 1H), 7.07 (td, J 8.4, 2.1 Hz, 2H), 6.94-6.24 (m, 2H), 4.24 (s, 2H), 2.49 (s, 3H), 2.25 (s, 3H), 2.09 (s, 3H). Method A HPLC-MS: MH+ m/z 500, RT 1.96 minutes (100%).

Workup

  1. stirringthe mixture was stirred at room temperature for 24 h
  2. stirringthe mixture was stirred for 3 days
  3. customThe solvent was removed
  4. customthe mixture was purified by silica gel chromatography
  5. washeluting with a 0-5% gradient of 7M ammonia/methanol in DCM

Sources & evidence

ORD record
ord-462ab880602047909c2c9b75c340bdb6
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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