Water → HCID 69459726, compound

HRID 1297112Notes

Reaction equation

HRID 1297112 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=3[NH:12][C:11](=[O:23])[CH2:10][N:9]=2)=[CH:4][CH:3]=1.[C:24]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[C:5]1([C:8]2[C:14]3[CH:15]=[C:16]([O:21][CH2:22][CH3:24])[C:17]([O:19][CH3:20])=[CH:18][C:13]=3[NH:12][C:11](=[O:23])[CH2:10][N:9]=2)[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 69461446HCID 69461446, compound

Product 1

HCID 69459726HCID 69459726, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg (0.267 mmol) of 5-(4-bromophenyl)-7,8-dimethoxy-1,3-dihydro-2H-1,4-benzodiazepin-2-one (XXIIaf) in 2 ml of anhydrous DMF, add under an inert atmosphere 48 mg (0.35 mmol) of K2CO3. After 30 minutes at room temperature, add dropwise 25 μl (0.4 mmol) of MeI. Allow to stand at room temperature for 12 hours. Add 30 ml of water. Extract three times with 30 ml of EtO2. Dry the organic fractions on Na2SO4. Purify by chromatography (AcOEt 1/hexane 1). Recrystallize in EtO2. One obtains 78 mg of the abovenamed product as a white powder. Yield: 73%. 1H-NMR (CDCl3, 200 MHz): d 3.40 (s, 3H, NCH3), 3.75 (s, 3H, OCH3), 3.99 (s, 3H, OCH3), 4.29 (AB system, ? d=1.014, JAB=10.7, 2H, CH2), 6.65 (s, 1H Ar), 6.78 (s, 1H Ar), 7.54 (s, 4H Ar).

Workup

  1. waitto stand at room temperature for 12 hours
  2. extractionExtract three times with 30 ml of EtO2
  3. customDry the organic fractions on Na2SO4
  4. customPurify by chromatography (AcOEt 1/hexane 1)
  5. customRecrystallize in EtO2

Sources & evidence

ORD record
ord-7868cda95dcc4f7fa801d34282821ccd
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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