Methyl Isocyanate → HCID 67051141, compound

HRID 2383222Notes

Reaction equation

HRID 2383222 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:29][NH2:30])[N:18]([CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:14]=2[C:13]2[CH:12]=[CH:11][C:10]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:9][C:8]=2[N:7]=1>CN(C=O)C>[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:29][NH:30][C:3]([NH:2][CH3:1])=[O:4])[N:18]([CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:25])[CH3:26])[C:14]=2[C:13]2[CH:12]=[CH:11][C:10]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:9][C:8]=2[N:7]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 67051110HCID 67051110, compound

Product 1

HCID 67051141HCID 67051141, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl isocyanate (322.9 mg, 5.66 mmol, 1.1 eq) was added to a solution of tert-butyl 2-(4-amino-2-aminomethyl-7-benzyloxy-1H-imidazo[4,5-c]quinolin-1-yl)ethylcarbamate (2.38 g, 5.14 mmol, 1 eq) in DMF and stirred at ambient temperature for 2 days. The crude reaction mixture was concentrated under reduced pressure and purified by flash column chromatography (on silica gel, 0-6% methanol in dichloromethane) and concentrated under reduced pressure to yield 2.73 g of tert-butyl 2-{4-amino-7-benzyloxy-2-[(3-methylureido)methyl]-1H-imidazo[4,5-c]quinolin-1-yl}ethylcarbamate.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. custompurified by flash column chromatography (on silica gel, 0-6% methanol in dichloromethane)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1e88047a7e644dd09e386b458b863e47
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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