Acetyl chloride → HCID 68463822, compound

HRID 501195Notes

Reaction equation

HRID 501195 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:24][CH2:23][C:14]3[NH:15][C:16]4[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:9][CH:10]=1)=[O:4].[H-].[Na+].[C:27](Cl)(=[O:29])[CH3:28]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:24][CH2:23][C:14]3[N:15]([C:27](=[O:29])[CH3:28])[C:16]4[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 68464048HCID 68464048, compound

Product 1

HCID 68463822HCID 68463822, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

From 8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole and Example 7 was obtained methyl-2-(8-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)pyrimidine-5-carboxylate using the method described in Example 12. To a solution of methyl-2-(8-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)pyrimidine-5-carboxylate (110 mg) in DMF (5 mL) was added sodium hydride (22 mg) at 0° C. and the mixtue was stirred for 20 min. Acetyl chloride (30 mg) was added and the reaction was allowed to attain room temperature and stirred another 3 hours. The reaction mixtue was partitioned between ethyl acetate and water. The organic layer was separated and washed with water and saturated aqueous sodium bicarbonate. The solvent was dried and evaporated and the residue purified by chromatography to give methyl-2-(5-acetyl-8-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)pyrimidine-5-carboxylate.

Workup

  1. customto attain room temperature
  2. stirringstirred another 3 hours
  3. customThe reaction mixtue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with water and saturated aqueous sodium bicarbonate
  6. customThe solvent was dried
  7. customevaporated
  8. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-618daf19eff94fdf9fb42da71a50a927
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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