Isopropyl isocyanate → HCID 58833649, compound

HRID 2203567Notes

Reaction equation

HRID 2203567 reaction equation
[CH:1]([N:4]=[C:5]=[O:6])([CH3:3])[CH3:2].[CH3:7][O:8][CH2:9][CH2:10][C:11]1[N:12]([CH2:32][CH2:33][CH3:34])[C:13]2[C:22]3[CH:21]=[CH:20][C:19]([O:23][CH:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)=[CH:18][C:17]=3[N:16]=[C:15]([NH2:30])[C:14]=2[N:31]=1>C(Cl)(Cl)Cl>[NH2:30][C:15]1[C:14]2[N:31]=[C:11]([CH2:10][CH2:9][O:8][CH3:7])[N:12]([CH2:32][CH2:33][CH3:34])[C:13]=2[C:22]2[CH:21]=[CH:20][C:19]([O:23][CH:24]3[CH2:29][CH2:28][N:27]([C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:26][CH2:25]3)=[CH:18][C:17]=2[N:16]=1

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 68972633HCID 68972633, compound

Product 1

HCID 58833649HCID 58833649, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Isopropyl isocyanate (0.256 mL, 2.61 mmol) was added dropwise to a stirred mixture of 2-(2-methoxyethyl)-7-(piperidin-4-yloxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-ylamine (1.00 g, 2.61 mmol) in chloroform at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred for 16 hours. The solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography (silica gel, gradient elution with 4-12% CMA in chloroform) followed by recrystallization from acetonitrile to afford 0.530 g of 4-{[4-amino-2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}-N-isopropylpiperidine-1-carboxamide as white crystals, mp 176-179° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe crude product was purified by flash chromatography (silica gel, gradient elution with 4-12% CMA in chloroform)
  3. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-6829b9895f4f415e8e7f9b29eee30940
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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