Methyl iodide → HCID 71183536, compound

HRID 2366581Notes

Reaction equation

HRID 2366581 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[C:13]2[CH:16]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)[CH:18]=[CH:19][C:12]=2[NH:11][C:10](=[O:30])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[CH2:1]([N:8]1[C:14](=[O:15])[C:13]2[CH:16]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)[CH:18]=[CH:19][C:12]=2[N:11]([CH3:31])[C:10](=[O:30])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 71183136HCID 71183136, compound

Product 1

HCID 71183536HCID 71183536, compoundYield 17.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-Benzyl-7-(4-(trifluoromethyl)phenyl)-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione (9.80 mg, 0.024 mmol) and K2CO3 (10 mg, 0.072 mmol, 3.0 equiv.) were placed in a 0.5-2 mL Smith process vial under a nitrogen atmosphere. To the vial were added DMF (0.5 mL) and iodomethane (2.25 μL, 0.036 mmol, d=2.28 g/cm3, 1.5 equiv) at room temperature. After heating, stirred, at 60° C. for 2 hours, the reaction mixture was concentrated en vacuo. The resulting crude mixture was diluted with acetonitrile (1 mL), filtered through a syringe filter and injected into a preparative HPLC to give desired product (4-benzyl-1-methyl-7-(4-(trifluoromethyl)phenyl)-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione, 1.8 mg) as a yellow film.

Workup

  1. temperatureAfter heating
  2. concentrationthe reaction mixture was concentrated en vacuo
  3. additionThe resulting crude mixture was diluted with acetonitrile (1 mL)
  4. filtrationfiltered through a syringe
  5. filtrationfilter

Sources & evidence

ORD record
ord-8b81c5863cd84779b6cf88edbcac43e7
Source dataset
uspto-grants-2014_04
Patent number
US08697863B2

Reaction notes

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