Methyl iodide → HCID 18466620, compound

HRID 2229349Notes

Reaction equation

[Br:1][C:2]1[CH:23]=[N:22][C:5]2[N:6]([CH2:20][CH3:21])[C:7]3[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:8]=3[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=1.[H-].[Na+].[CH3:26]I>CN(C=O)C.O>[Br:1][C:2]1[CH:23]=[N:22][C:5]2[N:6]([CH2:20][CH3:21])[C:7]3[N:15]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:13]=[CH:12][C:8]=3[N:9]([CH3:26])[C:10](=[O:11])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the 8-bromo-5,11-dihydro-11-ethyl-2-(trifluoromethyl)-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (200 mg, 0.52 mmol) in DMF (2.6 mL) was added NaH (20 mg, 0.78 mmol), and the mixture was heated to 50° C. for 30 min. The reaction mixture was cooled to room temperature and treated with MeI (97 μL, 1.56 mmol). After 16 h, the reaction mixture was diluted with water. The resulting mixture was extracted with EtOAc (3×). The combined organic layer was successively washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (hexane:EtOAc, 8.5:1.5) to give the title compound (110 mg 53% yield) as a white foam.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionThe resulting mixture was extracted with EtOAc (3×)
washThe combined organic layer was successively washed with water and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography (hexane:EtOAc, 8.5:1.5)

Sources & evidence

ORD record: ord-4a158d5128f040f8bfddada92f08309c
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420359B1

Reaction notes

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