Acetyl chloride → HCID 86607544, compound

HRID 501193Notes

Reaction equation

HRID 501193 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C:11]1[CH:12]=[N:13][C:14]([N:17]2[CH2:29][CH2:28][C:27]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][C:19]=3[CH2:18]2)=[N:15][CH:16]=1)=[O:10].[H-].[Na+].[C:32](Cl)(=[O:34])[CH3:33]>CN(C=O)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C:11]1[CH:12]=[N:13][C:14]([N:17]2[CH2:29][CH2:28][C:27]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([C:32](=[O:34])[CH3:33])[C:19]=3[CH2:18]2)=[N:15][CH:16]=1)=[O:10]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 86607545HCID 86607545, compound

Product 1

HCID 86607544HCID 86607544, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-(tetrahydro-2H-pyran-2-yloxy)-2-[1,3,4,9-tetrahydro-2H-b-carbolin-2-yl]pyrimidine-5-carboxamide (120 mg, mmol) in DMF (5 mL) was added sodium hydride (22 mg) at 0° C. and the mixture was stirred for 20 min. Acetyl chloride (30 mg, mmol) was added and the reaction was allowed to attain room temperature and stirred 3 hours. After completion, the reaction mixture was partitioned between EtOAc and water. The organic layer was separated and washed with water, saturated sodium bicarbonate and concentrated. Pure N-(tetrahydro-2H-pyran-2-yloxy)-2-[9-acetyl-1,3,4,9-tetrahydro-2H-b-carbolin-2-yl]pyrimidine-5-carboxamide (80 mg, 60% yield) was obtained by column chromatography m/e=436 (M+1).

Workup

  1. customto attain room temperature
  2. stirringstirred 3 hours
  3. customAfter completion, the reaction mixture was partitioned between EtOAc and water
  4. customThe organic layer was separated
  5. washwashed with water, saturated sodium bicarbonate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c6d3858cea484c9e8707f6692fee2282
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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