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-(3,4-dihydro-naphthalen-1-yl)-3-methyl-phenyl]-methanone

HRID 1794006Notes

Reaction equation

HRID 1794006 reaction equation
[C:1]1([C:11]2[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][C:12]=2[CH3:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]=1.[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:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH2:4][CH2:3][CH:2]=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 222197044-(3,4-Dihydro-naphthalen-1-yl)-3-methyl-benzoic acid

Product 1

HCID 9867363(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[4-(3,4-dihydro-naphthalen-1-yl)-3-methyl-phenyl]-methanoneYield 85.7%

Procedure

4-(3,4-Dihydro-naphthalen-1-yl)-3-methyl-benzoic acid of Step B (0.220 g, 0.832 mmol) and 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.169 g, 0.915 mmol) were reacted in the manner of Example 15, Step D. Purification by flash column chromatography on silica gel, eluting with 15% ethyl acetate in hexane, followed by recrystallization from petroleum ether afforded the title compound (0.307 g) as white crystals, m.p. 108° C.

Workup

  1. customPurification by flash column chromatography on silica gel
  2. washeluting with 15% ethyl acetate in hexane
  3. customfollowed by recrystallization from petroleum ether

Sources & evidence

ORD record
ord-3a5cae35458946d7800e4d8f809ca83c
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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