Methyl iodide → HCID 69172682, compound

HRID 2114862Notes

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+].I[CH3:39]>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])[CH3:39])[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

Conditions

Temperature: 0 °C

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 (0.54 g, 1.07 mmol) in anhydrous DMF (6 mL) was treated with sodium hydride (38 mg, 1.60 mmol). The resultant mixture was stirred at the same temperature for 30 minutes, and treated with iodomethane (0.23 g, 1.60 mmol). After stirring at 0° C. 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 to provide the titled compound.

Workup

concentrationthe product mixture was concentrated under vacuum
customThe residue was partitioned between chloroform and brine
extractionThe organic extract
dry with materialwas dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-359c3c27384f4d9c9d51882b1465b1d8
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435735B2

Reaction notes

Loading…