Triethylamine → (4-Cyclohexyl-phenyl)-(4H,10H-3a,5,9-triaza-benzo[f]azulen-9-yl)-methanone

HRID 2054146Notes

Reaction equation

HRID 2054146 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[C:10]=1[CH2:9][NH:8][C:7]1[CH:11]=[CH:12][CH:13]=[N:14][C:6]=1[CH2:5]2.[CH:15]1([C:21]2[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)CC)C>ClCCCl>[CH:15]1([C:21]2[CH:22]=[CH:23][C:24]([C:25]([N:8]3[CH2:9][C:10]4[N:4]([CH:3]=[CH:2][CH:1]=4)[CH2:5][C:6]4[N:14]=[CH:13][CH:12]=[CH:11][C:7]3=4)=[O:26])=[CH:28][CH:29]=2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16752034HCID 16752034, compoundHCID 218908474-Cyclohexylbenzoyl chloride

Product 1

HCID 10156072(4-Cyclohexyl-phenyl)-(4H,10H-3a,5,9-triaza-benzo[f]azulen-9-yl)-methanoneYield 39.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of the 9,10-dihydro-4H-3a,5,9-triaza-benzo[f]azulene of Step D (4.67 mmol), 4-cyclohexylbenzoyl chloride (4.90 mmol) and triethylamine (5.1 mmol) in 1,2-dichloroethane was refluxed for three days under nitrogen. The solvent was removed in vacuo and the residue chromatographed on silica gel eluting with a solvent gradient from 5 to 20% of ethyl acetate in hexane to provide the title compound as a tan solid (0.684 g), m.p. 150-152° C.

Workup

  1. temperaturewas refluxed for three days under nitrogen
  2. customThe solvent was removed in vacuo
  3. customthe residue chromatographed on silica gel eluting with a solvent gradient from 5 to 20% of ethyl acetate in hexane

Sources & evidence

ORD record
ord-217379c2778a40dc8199196fbaff8abc
Source dataset
uspto-grants-2008_02
Patent number
US07329653B2

Reaction notes

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