7,8-dimethoxy-1-phenyl-3,5-dihydro-4H-2,3-benzodiazepin-4-one → HCID 10158376, compound

HRID 1297086Notes

Reaction equation

HRID 1297086 reaction equation
CO[C:3]1C(OC)=CC2C(C3C=CC=CC=3)=NNC(=O)CC=2[CH:20]=1.[S:23]1[C:27]([C:28]2[C:34]3[CH:35]=[C:36]([O:42][CH2:43][CH3:44])[C:37]([O:39][CH2:40][CH3:41])=[CH:38][C:33]=3[CH2:32][C:31](=[O:45])[NH:30][N:29]=2)=[CH:26][C:25]2[CH:46]=[CH:47][CH:48]=[CH:49][C:24]1=2>>[S:23]1[C:27]([C:28]2[C:34]3[CH:35]=[C:36]([O:42][CH2:43][CH3:44])[C:37]([O:39][CH2:40][CH3:41])=[CH:38][C:33]=3[CH2:32][C:31](=[O:45])[N:30]([CH2:3][CH3:20])[N:29]=2)=[CH:26][C:25]2[CH:46]=[CH:47][CH:48]=[CH:49][C:24]1=2

Participants

3

Reactant 2

HCID 98609727,8-dimethoxy-1-phenyl-3,5-dihydro-4H-2,3-benzodiazepin-4-oneHCID 10271143HCID 10271143, compound

Product 1

HCID 10158376HCID 10158376, compoundYield 72%

Procedure

By replacing 7,8-dimethoxy-1-phenyl-3,5-dihydro-4H-2,3-benzodiazepin-4-one VIaa in example IIIag by 1-(2-benzo[b]thienyl)-7,8-diethoxy-3,5-dihydro-4H-2,3-benzodiazepin-4-one VIab and proceeding in the same manner, the abovenamed product is obtained. Yield: 72%. M: 100–103° C. 1H-NMR (200 MHz, CDCl3): d 1.26 (t, J=7.1, 3H, CH3), 1.44 (t, J=7.0, 3H, CH3), 1.52 (t, J=7.1, 3H, CH3), 3.29–3.56 (m, 2H, 5-CH2), 3.85–4.25 (m, 6H, 3×CH2CH3), 6.87 (s, 1H Ar), 7.15 (s, 1H Ar), 7.32–7.44 (m, 3H Ar), 7.71–7.89 (m, 2H Ar).

Workup

  1. customthe abovenamed product is obtained
  2. custom100–103° C

Sources & evidence

ORD record
ord-1623733408b64f458475da711cfb0b26
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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