10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine → HCID 10114060, compound

HRID 1794016Notes

Reaction equation

HRID 1794016 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[CH2:16][C:15]([CH3:18])([CH3:17])[CH2:14][C:13]([CH3:20])([CH3:19])[CH:12]=1)[C:5](O)=[O:6].[CH:21]1[CH:22]=[CH:23][N:24]2[CH2:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[NH:27][CH2:26][C:25]=12>>[CH:21]1[CH:22]=[CH:23][N:24]2[CH2:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[N:27]([C:5]([C:4]3[CH:8]=[CH:9][C:10]([C:11]4[CH2:16][C:15]([CH3:17])([CH3:18])[CH2:14][C:13]([CH3:20])([CH3:19])[CH:12]=4)=[C:2]([CH3:1])[CH:3]=3)=[O:6])[CH2:26][C:25]=12

Participants

3

Reactant 2

HCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 22219696HCID 22219696, compound

Product 1

HCID 10114060HCID 10114060, compoundYield 80.4%

Procedure

3-Methyl-4-(3,3,5,5-tetramethyl-cyclohex-1-en-1-yl)-benzoic acid of Step B (0.100 g, 0.349 mmol) and 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.071 g, 0.384 mmol) were reacted in the manner of Example 15, Step D. Purification by flash column chromatography on silica gel, eluting with 20% ethyl acetate in hexane, followed by recrystallization from petroleum ether afforded the title compound (0.123 g) as white crystals, m.p. 158° C.

Workup

  1. customPurification by flash column chromatography on silica gel
  2. washeluting with 20% ethyl acetate in hexane
  3. customfollowed by recrystallization from petroleum ether

Sources & evidence

ORD record
ord-fd22fcef0a3b4f0f99468ccfa734e2aa
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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