Isopropyl isocyanate → HCID 11618232, compound

HRID 1373966Notes

Reaction equation

HRID 1373966 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([NH2:19])[C:9]=2[N:8]=[C:7]1[CH2:20][O:21][CH2:22][CH3:23].[CH:24]([N:27]=[C:28]=[O:29])([CH3:26])[CH3:25]>C(Cl)Cl.CN(C)C=O>[NH2:19][C:10]1[C:9]2[N:8]=[C:7]([CH2:20][O:21][CH2:22][CH3:23])[N:6]([NH:5][CH2:4][CH2:3][CH2:2][NH:1][C:28]([NH:27][CH:24]([CH3:26])[CH3:25])=[O:29])[C:18]=2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=1

Participants

5

Reactant 2

HCID 61277Isopropyl isocyanateHCID 86594228HCID 86594228, compound

Product 1

HCID 11618232HCID 11618232, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N1-(3-aminopropyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (1.04 g, 3.31 mmol) in 30 mL of CH2Cl2 and 5 mL of N,N-dimethylformamide was placed under an atmosphere of nitrogen and slowly treated with isopropyl isocyanate (0.320 mL, 3.31 mmol). After 15 h, the reaction mixture was concentrated under reduced pressure to yield a yellow/orange foam. The foam was purified by chromatography (SiO2, 30% (80:18:2 CHCl3:MeOH: conc. ammonium hydroxide (NH4OH)) in CHCl3) to give an off-white solid. The solid was triturated with diethyl ether (Et2O) and collected by vacuum filtration to yield 1-(3-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]amino}propyl)-3-isopropylurea (0.603 g) as an off-white solid. mp 174–177° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.45 (d, J=8.1 Hz, 1H), 7.58 (d, J=8.2 Hz, 1H), 7.46–7.41 (m, 1H), 7.26–7.22 (m, 1H), 6.96 (t, J=5.5 Hz, 1H), 6.60 (s, 2H), 5.72 (t, J=5.5 Hz, 1H), 5.59 (d, J=7.7 Hz, 1H), 4.75 (s, 2H), 3.70–3.58 (m, 3H), 3.19–3.08 (m, 4H), 1.72–1.63 (m, 2H), 1.17 (t, J=7.0 Hz, 3H), 0.99 (d, J=6.5 Hz, 6H); 13C NMR (75 MHz, DMSO-d6) δ 157.8, 152.3, 149.5, 145.3, 132.4, 127.4, 126.1, 124.2, 121.2, 114.7, 65.9, 63.1, 50.2, 41.2, 37.4, 28.9, 23.6, 15.4; MS (APCI) m/z 400 (M+H)+; Anal. Calcd for C20H29N7O2: C, 60.13; H, 7.32; N, 24.54; Found: C, 59.94; H, 7.58; N, 24.45.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto yield a yellow/orange foam
  3. customThe foam was purified by chromatography (SiO2, 30% (80:18:2 CHCl3:MeOH: conc. ammonium hydroxide (NH4OH)) in CHCl3)
  4. customto give an off-white solid
  5. customThe solid was triturated with diethyl ether (Et2O)
  6. filtrationcollected by vacuum filtration

Sources & evidence

ORD record
ord-f8db21dfa79e4c78a8e6fd8eef5236a9
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

Loading…