Acetyl chloride → HCID 10049084, compound

HRID 1768479Notes

Reaction equation

HRID 1768479 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[F:17])[CH2:7][N:6]1[C:18]([N:20]([CH3:22])[CH3:21])=[O:19].C(N(CC)CC)C.[C:36](Cl)(=[O:38])[CH3:37]>C1COCC1>[C:36]([NH:1][CH2:2][CH2:3][CH2:4][C:5]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[F:17])[CH2:7][N:6]1[C:18]([N:20]([CH3:22])[CH3:21])=[O:19])(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 10001131HCID 10001131, compound

Product 1

HCID 10049084HCID 10049084, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 20 mg (0.05 mmol) of amine 20-2 in THF was added 21 μL (0.15 mmol) of triethylamine and 7 μL (0.10 mmol) of acetyl chloride. After stirring overnight the reaction was partitioned between EtOAc and 10% KHSO4, the organic phase was washed with saturated NaHCO3, brine, dried over MgSO4, and concentrated by rotary evaporation. The residue was purified by column chromatography on silica gel with EtOAc/hexanes to provide 20-3 as a white solid. Data for 20-3: 1HNMR (500 MHz, d6-DMSO) δ 7.8 (m, 1H), 7.6 (m, 1H), 7.4-7.2 (m, 7H), 6.2 (s, 1H), 4.9 (m, 1H), 4.7 (m, 1H), 3.05 (m, 2H), 2.7 (s, 6H), 2.05 (m, 1H), 1.8 (s, 3H), 1.2-1.1 (m, 3H) ppm. HRMS (ES) calc'd M+H for C24H27ClFN3O2: 444.1849. Found: 444.1847.

Workup

  1. customwas partitioned between EtOAc and 10% KHSO4
  2. washthe organic phase was washed with saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue was purified by column chromatography on silica gel with EtOAc/hexanes

Sources & evidence

ORD record
ord-17222e65f19947298ddaaf0fc891d964
Source dataset
uspto-grants-2007_06
Patent number
US07235580B2

Reaction notes

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