Acetyl chloride → HCID 67015710, compound

HRID 1618035Notes

Reaction equation

HRID 1618035 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH:5]1[CH2:8][CH:7]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[CH2:16][C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[CH:20]=3)=[O:18])=[CH:11][CH:10]=2)[CH2:6]1.C(N(CC)C(C)C)(C)C>ClCCl>[C:1]([N:5]1[CH2:8][CH:7]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[CH2:16][C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[CH:20]=3)=[O:18])=[CH:11][CH:10]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 67015698HCID 67015698, compound

Product 1

HCID 67015710HCID 67015710, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (30 mg) was added at room temperature to a solution of (R)-3-(4-(azetidin-3-yl)phenyl)-1-(2-methylpyridin-4-yl)-3-o-tolylpropan-1-one (example 482, step 1; 70 mg) and N,N-diisopropylethylamine (98 mg) in dichloromethane (4 mL), then after 2 h the reaction mixture was partitioned between sat. aq. sodium hydrogencarbonate solution and dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated. Flash chromatography (silica gel, 10 g, 2% to 5% methanol in dichlormethane) produced the title compound (19 mg). Colourless oil, MS (ESI+): m/z=413.0 [M+H]+.

Workup

  1. customafter 2 h the reaction mixture was partitioned between sat. aq. sodium hydrogencarbonate solution and dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-c96206451abb4f7c8fa1d43c83fcb3b5
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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