10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine → HCID 10273004, compound

HRID 1794004Notes

Reaction equation

HRID 1794004 reaction equation
[CH3:1][C:2]1([CH3:18])[C:7]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][C:9]=2[CH3:17])=[CH:6][CH2:5][CH2:4][CH2:3]1.[CH:19]1[CH:20]=[CH:21][N:22]2[CH2:28][C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[NH:25][CH2:24][C:23]=12>>[CH:19]1[CH:20]=[CH:21][N:22]2[CH2:28][C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[N:25]([C:12]([C:11]3[CH:15]=[CH:16][C:8]([C:7]4[C:2]([CH3:1])([CH3:18])[CH2:3][CH2:4][CH2:5][CH:6]=4)=[C:9]([CH3:17])[CH:10]=3)=[O:14])[CH2:24][C:23]=12

Participants

3

Reactant 2

HCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 22219702HCID 22219702, compound

Product 1

HCID 10273004HCID 10273004, compoundYield 51.2%

Procedure

4-(6,6-Dimethyl-cyclohex-1-en-1-yl)-3-methyl-benzoic acid of Step B (0.078 g, 0.319 mmol) and 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.065 g, 0.351 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 (0.0670 g) as white crystals, m.p. 131° 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-fc8175f18cf244fdab917d6ecbf33561
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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