Isopropyl isocyanate → HCID 58833649, compound

HRID 540892Notes

Reaction equation

HRID 540892 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-50caa5cf950640bc9b03885023ed36e3
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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