10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine → HCID 10202480, compound

HRID 1794014Notes

Reaction equation

HRID 1794014 reaction equation
[CH3:1][C:2]1([CH3:19])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH:5]=[C:6]2[C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=1[CH3:18].[CH:20]1[CH:21]=[CH:22][N:23]2[CH2:29][C:28]3[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=3[NH:26][CH2:25][C:24]=12>>[CH:20]1[CH:21]=[CH:22][N:23]2[CH2:29][C:28]3[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=3[N:26]([C:13]([C:12]3[CH:16]=[CH:17][C:9]([C:6]4[CH:7]5[CH2:8][CH:3]([CH2:4][CH:5]=4)[C:2]5([CH3:1])[CH3:19])=[C:10]([CH3:18])[CH:11]=3)=[O:14])[CH2:25][C:24]=12

Participants

3

Reactant 2

HCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 22219717HCID 22219717, compound

Product 1

HCID 10202480HCID 10202480, compoundYield 86.2%

Procedure

4-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-3-methyl-benzoic acid of Step B (0.360 g, 1.40 mmol) and 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.284 g, 1.54 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 ethyl acetate afforded the title compound (0.510 g) as white crystals, m.p. 187° C.

Workup

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

Sources & evidence

ORD record
ord-011952291b2240c88995595c3a4cd264
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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