Isopropyl isocyanate → HCID 58833694, compound

HRID 2203596Notes

Reaction equation

HRID 2203596 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:26][CH2:27][CH3:28])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([O:17][CH:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)=[CH:12][C:11]=3[N:10]=[C:9]([NH2:24])[C:8]=2[N:25]=1)[CH3:2].[CH:29]([N:32]=[C:33]=[O:34])([CH3:31])[CH3:30]>ClCCl>[NH2:24][C:9]1[C:8]2[N:25]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:6]([CH2:26][CH2:27][CH3:28])[C:7]=2[C:16]2[CH:15]=[CH:14][C:13]([O:17][CH:18]3[CH2:19][CH2:20][N:21]([C:33]([NH:32][CH:29]([CH3:31])[CH3:30])=[O:34])[CH2:22][CH2:23]3)=[CH:12][C:11]=2[N:10]=1

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 58833655HCID 58833655, compound

Product 1

HCID 58833694HCID 58833694, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(Ethoxymethyl)-7-(piperidin-4-yloxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine (0.500 g, 1.3 mmol) was slurried in dichloromethane (13 mL). Isopropyl isocyanate was added dropwise to the slurry and the reaction was stirred for 16 hours. The reaction was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 2-22% CMA in chloroform) followed by recrystallization from acetonitrile yielded 0.430 g of 4-{[4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}-N-isopropylpiperidine-1-carboxamide as a white solid, mp 163-164.5° C.

Workup

  1. customThe reaction was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 2-22% CMA in chloroform)
  2. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-539b35e8570d458784cc128d65658658
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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