N-(2,6-Dichloro-5-quinolinyl)-cyclohexaneacetamide → N-[6-Chloro-2-[3-[(3-hydroxypropyl)amino]propyl]-5-quinolinyl]-cyclohexaneacetamide

HRID 2217815Notes

Reaction equation

HRID 2217815 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:22])[C:8]=2[NH:12][C:13](=[O:21])[CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[N:3]=1.CC([Si](C)(C)[O:28][CH2:29][CH2:30][CH2:31][N:32]([CH2:40][CH:41]=[CH2:42])C(=O)OC(C)(C)C)(C)C>>[Cl:22][C:7]1[C:8]([NH:12][C:13](=[O:21])[CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH2:42][CH2:41][CH2:40][NH:32][CH2:31][CH2:30][CH2:29][OH:28])[CH:11]=[CH:10]2

Participants

3

Reactant 2

HCID 86012996N-(2,6-Dichloro-5-quinolinyl)-cyclohexaneacetamideHCID 86595927Tert-butyl allyl(3-(tert-butyldimethylsilyloxy)propyl)carbamate

Product 1

HCID 11750436N-[6-Chloro-2-[3-[(3-hydroxypropyl)amino]propyl]-5-quinolinyl]-cyclohexaneacetamideYield 13%

Procedure

Prepared according to the method of example 1(b)/(c), using N-(2,6-dichloro-5-quinolinyl)-cyclohexaneacetamide (Example 1(a)) (130 mg) and [3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]-2-propenyl-carbamic acid, 1,1-dimethylethyl ester (example 22(a)) (152 mg). Purification (SiO2, methanol:dichloromethane 1:9 as eluant) gave the title compound as a colourless solid (21 mg).

Workup

  1. customPrepared
  2. customPurification (SiO2, methanol:dichloromethane 1:9 as eluant)

Sources & evidence

ORD record
ord-f6d8cd73edef48fb90d12684422ffc10
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

Loading…