Ethyl isocyanate → HCID 11574556, compound

HRID 1373981Notes

Reaction equation

HRID 1373981 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].[CH2:24]([N:26]=[C:27]=[O:28])[CH3:25]>C(Cl)Cl>[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:27]([NH:26][CH2:24][CH3:25])=[O:28])[C:18]=2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 86594228HCID 86594228, compound

Product 1

HCID 11574556HCID 11574556, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N1-(3-aminopropyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (1.42 g, 4.52 mmol) in 25 mL of CH2Cl2 was placed under an atmosphere of nitrogen and chilled in an ice water bath. The solution was slowly treated with ethyl isocyanate (0.375 mL, 4.74 mmol). Upon addition the reaction mixture became thick and additional CH2Cl2 had to be added to keep the mixture stirring. The reaction was allowed to slowly warm to ambient temperature. After 17 h, the reaction was concentrated under reduced pressure to yield an off-white solid. The solid was purified by chromatography (SiO2, 15–50% (80:18:2 CHCl3:MeOH:NH4OH) in CHCl3) to yield an off-white solid. The solid was recrystallized from MeCN to give 1-(3-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]amino}propyl)-3-ethylurea (1.16 g) as a white solid. mp 138–141° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.45 (dd, J=8.1, 1.0 Hz, 1H), 7.58 (dd, J=8.3, 0.9 Hz, 1H), 7.46–7.41 (m, 1H), 7.27–7.21 (m, 1H), 6.96 (t, J=5.6 Hz, 1H), 6.60 (s, 2H), 5.83 (t, J=5.7 Hz, 1H), 5.73 (t, J=5.5 Hz, 1H), 4.75 (s, 2H), 3.61 (q, J=7.0 Hz, 2H), 3.20–3.08 (m, 4H), 3.03–2.94 (m, 2H), 1.68 (p, J=6.9 Hz, 2H), 1.17 (t, J=7.0 Hz, 3H), 0.96 (t, J=7.1 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 158.4, 152.3, 149.5, 145.3, 132.4, 127.4, 126.1, 124.2, 121.3, 121.2, 114.8, 65.9, 63.1, 50.2, 37.6, 34.4, 28.9, 16.0, 15.4; MS (ESI) m/z 386 (M+H)+; Anal. Calcd for C19H27N7O2•0.5H2O: C, 57.85; H, 7.15; N, 24.85; Found: C, 57.84; H, 7.31; N, 25.04.

Workup

  1. temperaturechilled in an ice water bath
  2. additionUpon addition the reaction mixture
  3. additionto be added
  4. concentrationthe reaction was concentrated under reduced pressure
  5. customto yield an off-white solid
  6. customThe solid was purified by chromatography (SiO2, 15–50% (80:18:2 CHCl3:MeOH:NH4OH) in CHCl3)
  7. customto yield an off-white solid
  8. customThe solid was recrystallized from MeCN

Sources & evidence

ORD record
ord-d3f6e7eccdd14d3bbe451b5457b0849d
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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