10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine → 10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl-(4-cyclohex-1-enyl-3-methyl-phenyl)-methanone

HRID 1794001Notes

Reaction equation

HRID 1794001 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][C:8]=2[CH3:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH:17]1[CH:18]=[CH:19][N:20]2[CH2:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[NH:23][CH2:22][C:21]=12>>[CH:17]1[CH:18]=[CH:19][N:20]2[CH2:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[N:23]([C:11]([C:10]3[CH:14]=[CH:15][C:7]([C:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=4)=[C:8]([CH3:16])[CH:9]=3)=[O:13])[CH2:22][C:21]=12

Participants

3

Reactant 2

HCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 222197134-Cyclohex-1-en-1-yl-3-methyl-benzoic acid

Product 1

HCID 1022151510,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl-(4-cyclohex-1-enyl-3-methyl-phenyl)-methanoneYield 80.3%

Procedure

4-Cyclohex-1-en-1-yl-3-methyl-benzoic acid of Step C (0.360 g, 1.66 mmol) and 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.337 g, 1.83 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 1:1 ethyl acetate/petroleum ether afforded the title compound (0.510 g) as white crystals, m.p. 182–183° C.

Workup

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

Sources & evidence

ORD record
ord-21485b4fde0f4b969e1d1e4e829061ee
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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