Water → HCID 68931533, compound

HRID 1260988Notes

Reaction equation

HRID 1260988 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:14]([N:15]([CH3:28])[C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=3)=[O:17])[CH2:13][CH2:12][N:11]([C:29]([C:31]3[NH:32][C:33]4[C:34](=[O:40])[CH2:35][CH2:36][CH2:37][C:38]=4[CH:39]=3)=[O:30])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].[CH3:43]I.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:14]([N:15]([CH3:28])[C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:26])([F:25])[F:27])=[CH:20][N:19]=3)=[O:17])[CH2:13][CH2:12][N:11]([C:29]([C:31]3[N:32]([CH3:43])[C:33]4[C:34](=[O:40])[CH2:35][CH2:36][CH2:37][C:38]=4[CH:39]=3)=[O:30])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68936688HCID 68936688, compound

Product 1

HCID 68931533HCID 68931533, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound (0.060 g) obtained in Example 642 in DMF (1 mL) was added sodium hydride (0.005 g) and the mixture was stirred for 10 min. Methyl iodide (0.020 mL) was added at 0° C. and the mixture was stirred at room temperature. To the reaction mixture was added water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH Chromatorex) (solvent gradient; 30→70% ethyl acetate/hexane) to give the title compound (0.020 g, 33%) as a white powder.

Workup

  1. stirringthe mixture was stirred at room temperature
  2. extractionthe resultant product was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (NH Chromatorex) (solvent gradient; 30→70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-74277777865045dc8f72a09524b1d792
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

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