Cyclohexyl isocyanate → HCID 58833613, compound

HRID 540906Notes

Reaction equation

HRID 540906 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>ClCCl>[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, compound2×

Product 1

HCID 58833613HCID 58833613, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The preparation of 2-methyl-1-(2-methylpropyl)-7-(2-piperidin-4-ylethoxy)-1H-imidazo[4,5-c]quinolin-4-amine is described in Example 24. Cyclohexyl isocyanate (0.100 mL, 0.786 mmol) was added dropwise to a stirred 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 dichloromethane (10 mL) at 0° C. After 30 minutes, the solution was concentrated under reduced pressure and the resulting residue was purified by flash chromatography (silica gel, sequential elution with 2% and 5% methanol in dichloromethane) followed by recrystallization from ethanol to afford 0.141 g of 4-{2-[(4-amino-1-isobutyl-2-methyl-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. concentrationthe solution was concentrated under reduced pressure
  2. customthe resulting residue was purified by flash chromatography (silica gel, sequential elution with 2% and 5% methanol in dichloromethane)
  3. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-5e8adf83e2dc46019018bf162326e8cb
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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