Sodium hydride → HCID 69171007, compound

HRID 2114860Notes

Reaction equation

HRID 2114860 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:5][N:6]1[CH:20]=[C:19]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:18]2[N:11]3[CH2:12][CH2:13][N:14]([CH3:17])[C:15](=[O:16])[C:10]3=[C:9]([O:29][CH3:30])[C:8]=2[C:7]1=[O:31].[H-].[Na+].[CH3:38][S:39](Cl)(=[O:41])=[O:40]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:5][N:6]1[CH:20]=[C:19]([N:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[S:39]([CH3:38])(=[O:41])=[O:40])[C:18]2[N:11]3[CH2:12][CH2:13][N:14]([CH3:17])[C:15](=[O:16])[C:10]3=[C:9]([O:29][CH3:30])[C:8]=2[C:7]1=[O:31]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 69171435HCID 69171435, compound

Product 1

HCID 69171007HCID 69171007, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A cold (0° C.) solution of 2-(3-chloro-4-fluorobenzyl)-10-methoxy-4-(N-tert-butoxylcarbonyl-amino)-8-methyl-7,8-dihydropyrido-[3′,4′:4,5]pyrrolo[1,2-a]pyrazine-1,9(2H,6H)-dione (0.74 g, 1.70 mmol) in anhydrous DMF (3 mL) was treated with sodium hydride (7 mg, 0.30 mmol). The resultant mixture was stirred at the same temperature for 30 minutes, and treated with methanesulfonyl chloride (34 mg, 0.30 mmol). After stirring at 0° for 1 hour, the product mixture was concentrated under vacuum. The residue was partitioned between chloroform and brine. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 20% methanol in ethyl acetate. Collection and concentration of appropriate fractions provided the titled compound.

Workup

  1. concentrationthe product mixture was concentrated under vacuum
  2. customThe residue was partitioned between chloroform and brine
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-2d1f5a8128a24eaab41bb6fa81c08bd2
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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