Methyl iodide → HCID 10840499, compound

HRID 1081316Notes

Reaction equation

HRID 1081316 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:6][N:7]([CH3:29])[C:8]([C:10]1[N:19]([CH3:20])[C:18](=[O:21])[C:17]2[CH2:16][CH2:15][CH2:14][NH:13][C:12]=2[C:11]=1[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)=[O:9].[H-].[Na+].IC.[C:43](OCC)(=O)C>C1COCC1>[F:38][C:2]([F:37])([F:1])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:34])([F:36])[F:35])[CH:32]=1)[CH2:6][N:7]([CH3:29])[C:8]([C:10]1[N:19]([CH3:20])[C:18](=[O:21])[C:17]2[CH2:16][CH2:15][CH2:14][N:13]([CH3:43])[C:12]=2[C:11]=1[C:22]1[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=1)=[O:9]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 10459957HCID 10459957, compound

Product 1

HCID 10840499HCID 10840499, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (3 ml) was dissolved N-[3,5-bis(trifluoro methyl)benzyl]-8-(4-fluorophenyl)-1,2,3,4,5,6-hexahydro-N,6-dimethyl-5-oxo-7-pyrido[4,3-b]pyridinecarboxamide (Example 27)(68 mg). To the solution were added sodium hydride (60% oil) (6 mg) and iodomethane (1.5 ml). The mixture was stirred for 15 hours at room temperature. To the reaction mixture was added ethyl acetate, and the mixture was washed with water and dried, then the solvent was distilled off to give the above-titled compound as colorless crystals (39 mg), m.p.230°-232° C. (recrystallized from ethyl acetate-ethyl ether)

Workup

  1. washthe mixture was washed with water
  2. customdried
  3. distillationthe solvent was distilled off
  4. customto give
  5. customthe above-titled compound as colorless crystals (39 mg), m.p.230°-232° C. (recrystallized from ethyl acetate-ethyl ether)

Sources & evidence

ORD record
ord-68b3158e3f19436fbd5ee39ec1788bfd
Source dataset
uspto-grants-1996_12
Patent number
US05585385

Reaction notes

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