10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine → HCID 10157606, compound

HRID 1793988Notes

Reaction equation

HRID 1793988 reaction equation
[CH3:1][C:2]1([CH3:17])[C:7]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)=[CH:6][CH2:5][CH2:4][CH2:3]1.[CH:18]1[CH:19]=[CH:20][N:21]2[CH2:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[NH:24][CH2:23][C:22]=12>>[CH:18]1[CH:19]=[CH:20][N:21]2[CH2:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[N:24]([C:12]([C:11]3[CH:10]=[CH:9][C:8]([C:7]4[C:2]([CH3:1])([CH3:17])[CH2:3][CH2:4][CH2:5][CH:6]=4)=[CH:16][CH:15]=3)=[O:14])[CH2:23][C:22]=12

Participants

3

Reactant 2

HCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 22219698HCID 22219698, compound

Product 1

HCID 10157606HCID 10157606, compoundYield 85.5%

Procedure

4-(6,6-Dimethyl-cyclohex-1-en-1-yl)-benzoic acid of Step B (0.235 g, 1.02 mmol) and 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.205 g, 1.11 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 (0.346 g) as white crystals, m.p. 118° 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-978fe234b6694dc898dc6657e05d2509
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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