Isopropyl isocyanate → HCID 58869077, compound

HRID 1623139Notes

Reaction equation

HRID 1623139 reaction equation
[CH:1]([N:4]=[C:5]=[O:6])([CH3:3])[CH3:2].[NH2:7][C:8]1[C:17]2[N:18]=[C:19]([CH2:29][CH2:30][CH3:31])[N:20]([CH2:21][CH2:22][CH2:23][CH:24]([NH:26][O:27][CH3:28])[CH3:25])[C:16]=2[C:15]2[CH:14]=[CH:13][C:12]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:11][C:10]=2[N:9]=1>>[NH2:7][C:8]1[C:17]2[N:18]=[C:19]([CH2:29][CH2:30][CH3:31])[N:20]([CH2:21][CH2:22][CH2:23][CH:24]([N:26]([O:27][CH3:28])[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH3:25])[C:16]=2[C:15]2[CH:14]=[CH:13][C:12]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[CH:11][C:10]=2[N:9]=1

Participants

3

Reactant 2

HCID 61277Isopropyl isocyanateHCID 86612257HCID 86612257, compound

Product 1

HCID 58869077HCID 58869077, compound

Procedure

Isopropyl isocyanate (0.35 mL, 3.58 mmol) was added to a solution of N-[4-(4-amino-7-phenyl-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-methylbutyl]-O-methylhydroxylamine (1.25 g, 2.99 mmol) and stirred at ambient temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and purified by flash column chromatography on silica gel (eluting with 5% methanol in dichloromethane) to provide 1-[4-(4-amino-7-phenyl-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-methylbutyl]-3-isopropyl-1-methoxyurea as a tan powder, mp 101-103° C. MS (APCI) m/z 503.3 (M+H+); Anal. calcd for C29H38N6O2 0.85H2O: C, 67.25; H, 7.73; N, 16.22. Found: C, 66.84; H, 7.64; N, 15.89.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by flash column chromatography on silica gel (eluting with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e975ebf5891d4ae0864cfb96e540d5c1
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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