Triethylamine → HCID 178476475, compound

HRID 237339Notes

Reaction equation

HRID 237339 reaction equation
Cl.[Cl:2][C:3]1[CH:26]=[CH:25][C:6]2[N:7]3[C:11]([CH2:12][NH:13][CH2:14][C:5]=2[CH:4]=1)=[N:10][N:9]=[C:8]3[C@H:15]1[CH2:20][CH2:19][C@H:18]([O:21][CH:22]([CH3:24])[CH3:23])[CH2:17][CH2:16]1.C(N(CC)CC)C.[C:34]([O:37][CH2:38][C:39](Cl)=[O:40])(=[O:36])[CH3:35]>ClCCl>[Cl:2][C:3]1[CH:26]=[CH:25][C:6]2[N:7]3[C:11](=[N:10][N:9]=[C:8]3[C@H:15]3[CH2:16][CH2:17][C@H:18]([O:21][CH:22]([CH3:24])[CH3:23])[CH2:19][CH2:20]3)[CH2:12][N:13]([C:39](=[O:40])[CH2:38][O:37][C:34](=[O:36])[CH3:35])[CH2:14][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 178459238HCID 178459238, compound

Product 1

HCID 178476475HCID 178476475, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of trans-8-chloro-1-(4-isopropoxy-cyclohexyl)-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene hydrochloride (0.090 g, 0.23 mmol) and triethylamine (0.066 ml, 0.48 mmol) in dichloromethane (5 ml) was added acetoxy acetyl chloride (0.031 g, 0.25 mmol) at room temperature. After stirring for 19 h the reaction mixture was concentrated in vacuo. Flash-chromatography with n-heptane/2-propanol as eluent gave the title compound (0.073 g, 70%) as white solid. MS m/e: 461 (M+H+).

Workup

  1. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-3b02779045da49dd82a817f68508b9e8
Source dataset
uspto-grants-2014_02
Patent number
US08642590B2

Reaction notes

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