Water → HCID 9902426, compound

HRID 1297083Notes

Reaction equation

HRID 1297083 reaction equation
I[CH2:2][CH2:3][CH3:4].[CH3:5][O:6][C:7]1[C:8]([O:25][CH3:26])=[CH:9][C:10]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][NH:14][C:13](=[O:23])[CH2:12][C:11]=2[CH:24]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:5][O:6][C:7]1[C:8]([O:25][CH3:26])=[CH:9][C:10]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][N:14]([CH2:2][CH2:3][CH3:4])[C:13](=[O:23])[CH2:12][C:11]=2[CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 98609727,8-dimethoxy-1-phenyl-3,5-dihydro-4H-2,3-benzodiazepin-4-one

Product 1

HCID 9902426HCID 9902426, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add dropwise under an inert atmosphere 400 μl of iodopropane to a solution of 200 mg (0.675 mmol) of 7,8-dimethoxy-1-phenyl-3,5-dihydro-4H-2,3-benzodiazepin-4-one VIaa and 121 mg (0.878 mmol) of K2CO3 in solution in 5 ml of DMF. After 72 hours at room temperature, add 30 ml of H2O and extract three times with 30 ml of Et2O. Dry the organic fractions on Na2SO4. Purify by chromatography (AcOEt 1/hexane 1). Yield: 72%. M: 48–52° C. 1H-NMR (300 MHz, CDCl3): d 0.83 (t, J=7.34, 3H, CH3), 1.65–1.72 (m, 2H, CH2CH3), 2.85–3.62 (m, 4H, CH2CH2CH3+5-CH2), 3.74 (s, 3H, OCH3), 3.98 (s, 3H, OCH3), 6.67 (s, 1H Ar), 6.89 (s, 1H Ar), 7.43–7.47 (m, 3H Ar), 7.65–7.68 (m, 2H Ar).

Workup

  1. extractionextract three times with 30 ml of Et2O
  2. customDry the organic fractions on Na2SO4
  3. customPurify by chromatography (AcOEt 1/hexane 1)
  4. custom48–52° C

Sources & evidence

ORD record
ord-4f649cc348df4d9cb02272904c82c0e5
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

Loading…