Triethylamine → HCID 18449089, compound

HRID 1270176Notes

Reaction equation

HRID 1270176 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:18]=[CH:17][C:8]2[CH2:9][N:10]3[CH:16]=[CH:15][CH:14]=[C:11]3[CH2:12][NH:13][C:7]=2[CH:6]=1)=[O:4].[CH:19]1([C:25]2[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(N(CC)CC)C>ClCCCl>[CH:19]1([C:25]2[CH:26]=[CH:27][C:28]([C:29]([N:13]3[C:7]4[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:18]=[CH:17][C:8]=4[CH2:9][N:10]4[CH:16]=[CH:15][CH:14]=[C:11]4[CH2:12]3)=[O:30])=[CH:32][CH:33]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 218908474-Cyclohexylbenzoyl chlorideHCID 22053625HCID 22053625, compound

Product 1

HCID 18449089HCID 18449089, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-8-carboxylic acid methyl ester of Step B (9.9 mmol) in 1,2-dichloroethane (25 mL) was added 4-cyclohexyl benzoyl chloride (1.1 equiv.) and triethylamine (2.5 equiv.) and the mixture was stirred at room temperature overnight. The solvent was then removed in vacuo and the residue chromatographed on silica gel eluting with 5% ethyl acetate in petroleum ether to provide the title compound as a white crystalline solid, m.p. 174–176° C.

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue chromatographed on silica gel eluting with 5% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-c36d06bbe1474a3094195ba86689cc12
Source dataset
uspto-grants-2007_04
Patent number
US07202239B2

Reaction notes

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