10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine → HCID 10158385, compound

HRID 1794012Notes

Reaction equation

HRID 1794012 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][C:10]=1[CH3:18].[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: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)=[C:10]([CH3:18])[CH:11]=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 22219699HCID 22219699, compound

Product 1

HCID 10158385HCID 10158385, compoundYield 68.3%

Procedure

4-(Bicyclo[3.2.1]oct-2-en-2-yl)-3-methyl-benzoic acid of Step B (0.132 g, 0.545 mmol) and 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.111 g, 0.6 mmol) were reacted by 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 (0.152 g) as white crystals, m.p. 168–169° 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-4ef7c0d631e145d89333edf1288aef03
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

Loading…