Isopropyl isocyanate → HCID 58833694, compound

HRID 540921Notes

Reaction equation

HRID 540921 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-4d9c1d1c0e2b4eee983faf494204f51a
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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