HCID 10224073, compound → HCID 10137937, compound

HRID 1297088Notes

Reaction equation

HRID 1297088 reaction equation
S1C(C2C3C=C(OCC)C(OCC)=CC=3CC(=O)NN=2)=CC2C=CC=C[C:2]1=2.[S:28]1[C:32]([C:33]2[C:39]3[CH:40]=[C:41]([O:47][CH2:48][CH3:49])[C:42]([O:44][CH2:45][CH3:46])=[CH:43][C:38]=3[CH:37]([CH2:50][CH2:51][CH3:52])[C:36](=[O:53])[NH:35][N:34]=2)=[CH:31][C:30]2[CH:54]=[CH:55][CH:56]=[CH:57][C:29]1=2>>[S:28]1[C:32]([C:33]2[C:39]3[CH:40]=[C:41]([O:47][CH2:48][CH3:49])[C:42]([O:44][CH2:45][CH3:46])=[CH:43][C:38]=3[CH:37]([CH2:50][CH2:51][CH3:52])[C:36](=[O:53])[N:35]([CH3:2])[N:34]=2)=[CH:31][C:30]2[CH:54]=[CH:55][CH:56]=[CH:57][C:29]1=2

Participants

3

Reactant 2

HCID 10224073HCID 10224073, compoundHCID 10271143HCID 10271143, compound

Product 1

HCID 10137937HCID 10137937, compoundYield 34%

Procedure

By replacing 1-(2-benzo[b]thienyl)-7,8-diethoxy-3,5-dihydro-4H-2,3-benzodiazepin-4-one VIab in example IIIba by 1-(2-benzo[b]thienyl)-7,8-diethoxy-5-n-propyl-3,5-dihydro-4H-2,3-benzodiazepin-4-one VIac and proceeding in the same manner, the abovenamed product is obtained. Yield: 34%. M: 61–63° C. 1H-NMR (200 MHz, CDCl3): d 1.01 (t, J=7.34, 3H, (CH2)2CH3), 1.39–4.55 (m, 8H, CH2CH2CH3+2×OCH2CH3), 1.75–2.42 (m, 2H, CH2CH2CH3), 3.04–3.11 (m, 1H, 5-H), 3.45 (s, 3H, 3-CH3), 3.99–4.23 (m, 4H, 2×OCH2CH3), 6.83 (s, 1H Ar), 7.12 (s, 1H Ar), 7.35–7.44 (m, 3H Ar), 7.72–7.89 (m, 2H Ar).

Workup

  1. customthe abovenamed product is obtained
  2. custom61–63° C

Sources & evidence

ORD record
ord-ddd97ba0a68944f694510c08c280b47f
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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