Cyclohexyl isocyanate → HCID 58833613, compound

HRID 2203514Notes

Reaction equation

HRID 2203514 reaction equation
[CH3:1][C:2]1[N:3]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:4]2[C:13]3[CH:12]=[CH:11][C:10]([O:14][CH2:15][CH2:16][CH:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)=[CH:9][C:8]=3[N:7]=[C:6]([NH2:23])[C:5]=2[N:24]=1.[CH:29]1([N:35]=[C:36]=[O:37])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>C(Cl)(Cl)Cl>[NH2:23][C:6]1[C:5]2[N:24]=[C:2]([CH3:1])[N:3]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:4]=2[C:13]2[CH:12]=[CH:11][C:10]([O:14][CH2:15][CH2:16][CH:17]3[CH2:18][CH2:19][N:20]([C:36]([NH:35][CH:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)=[O:37])[CH2:21][CH2:22]3)=[CH:9][C:8]=2[N:7]=1

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 58833624HCID 58833624, compound

Product 1

HCID 58833613HCID 58833613, compoundYield 32.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-methyl-1-(2-methylpropyl)-7-(2-piperidin-4-ylethoxy)-1H-imidazo[4,5-c]quinolin-4-amine (0.300 g, 0.786 mmol) in chloroform was cooled to 0° C. Cyclohexyl isocyanate (0.100 mL, 0.783 mmol) was added dropwise, and the reaction was stirred for 30 minutes. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluting with dichloromethane:methanol ranging in ratios from 99:1 to 95:5). The resulting product was recrystallized from ethanol to provide 0.130 g of 4-(2-{[4-amino-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethyl)-N-cyclohexylpiperidine-1-carboxamide as a white powder, mp 213.7-215.7° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (eluting with dichloromethane:methanol ranging in ratios from 99:1 to 95:5)
  3. customThe resulting product was recrystallized from ethanol

Sources & evidence

ORD record
ord-c2ac91d5059e48edb5c210ab141b6c7c
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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