10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine → HCID 10179649, compound

HRID 1793997Notes

Reaction equation

HRID 1793997 reaction equation
[CH3:1][C:2]1([CH3:18])[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][CH:10]=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: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([CH3:18])[CH3:1])=[CH:10][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 22219701HCID 22219701, compound

Product 1

HCID 10179649HCID 10179649, compoundYield 74.2%

Procedure

4-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-benzoic acid of Step B (0.160 g, 0.66 mmol) and 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.134 g, 0.726 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 (0.200 g) as white crystals, m.p. 118–119° 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-9b6517ca3ee7423c820c9c9912344e01
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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