10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine → HCID 10181649, compound

HRID 1794010Notes

Reaction equation

HRID 1794010 reaction equation
[C:1]([CH:5]1[C:10]([C:11]2[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][C:12]=2[CH3:20])=[CH:9][CH2:8][CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH:21]1[CH:22]=[CH:23][N:24]2[CH2:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[NH:27][CH2:26][C:25]=12>>[CH:21]1[CH:22]=[CH:23][N:24]2[CH2:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[N:27]([C:15]([C:14]3[CH:18]=[CH:19][C:11]([C:10]4[CH:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:6][CH2:7][CH2:8][CH:9]=4)=[C:12]([CH3:20])[CH:13]=3)=[O:16])[CH2:26][C:25]=12

Participants

3

Reactant 2

HCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 22219707HCID 22219707, compound

Product 1

HCID 10181649HCID 10181649, compoundYield 95.5%

Procedure

4-(6-tert-Butyl-cyclohex-1-en-1-yl)-3-methyl-benzoic acid of Step B (0.104 g, 0.382 mmol) and 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.077 g, 0.420 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 pentane afforded the title compound (0.160 g) as white crystals, m.p. 127–129° C.

Workup

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

Sources & evidence

ORD record
ord-ed3ee647fc334e39adea4a2e0dfb0739
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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