10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine → HCID 22219715, compound

HRID 1794018Notes

Reaction equation

HRID 1794018 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:15]2[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][C:16]=2[CH3:24])[CH:6]=[CH:7][CH:8]=1.[CH:25]1[CH:26]=[CH:27][N:28]2[CH2:34][C:33]3[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=3[NH:31][CH2:30][C:29]=12>>[CH:25]1[CH:26]=[CH:27][N:28]2[CH2:34][C:33]3[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=3[N:31]([C:19]([C:18]3[CH:22]=[CH:23][C:15]([C:10]4[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=4[C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=4)=[C:16]([CH3:24])[CH:17]=3)=[O:20])[CH2:30][C:29]=12

Participants

3

Reactant 2

HCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 22219694HCID 22219694, compound

Product 1

HCID 22219715HCID 22219715, compoundYield 62.9%

Procedure

4-[2-(3-Methoxy-phenyl)-cyclohex-1-en-1-yl]-3-methyl-benzoic acid of Step B (0.066 g, 0.205 mmol) and 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.041 g, 0.223 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/diethyl ether afforded the title compound (0.063 g) as white crystals, m.p. 91–94° 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/diethyl ether

Sources & evidence

ORD record
ord-34c37e7000814711beafb0dcc45a6331
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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