10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine → HCID 10135271, compound

HRID 1793995Notes

Reaction equation

HRID 1793995 reaction equation
[CH:1]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]=[C:2]2[C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=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:13]([C:12]3[CH:16]=[CH:17][C:9]([C:2]4[CH:1]5[CH2:8][CH:5]([CH2:4][CH:3]=4)[CH2:6][CH2:7]5)=[CH:10][CH:11]=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 22219712HCID 22219712, compound

Product 1

HCID 10135271HCID 10135271, compoundYield 86.1%

Procedure

4-Bicyclo[3.2.1]oct-2-en-2-yl-benzoic acid of Step B (0.270 g, 1.18 mmol) and 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.240 g, 1.30 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 (0.401 g) as white crystals, m.p. 157° 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-b5d2590f347a4f8ab8389caca07ab3e6
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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