Ethyl orthopropionate → HCID 11673425, compound

HRID 1373979Notes

Reaction equation

HRID 1373979 reaction equation
C(C(O)=O)(C)(C)C.NC1C=NC2C(C=1NN)=CC=CC=2.[CH:21]([NH:24][N:25]1[C:37]2[C:36]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[N:30]=[C:29]([NH2:38])[C:28]=2[N:27]=[C:26]1[CH2:39][CH2:40]C)([CH3:23])[CH3:22].C(OCC)(OCC)(OCC)CC.C(OC)(OC)(OC)CCC>>[CH2:39]([C:26]1[N:25]([NH:24][CH:21]([CH3:22])[CH3:23])[C:37]2[C:36]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[N:30]=[C:29]([NH2:38])[C:28]=2[N:27]=1)[CH3:40]

Participants

5

Reactant 4

HCID 66995Ethyl orthopropionateHCID 1235121,1,1-TrimethoxybutaneHCID 10423967HCID 10423967, compoundHCID 21075794HCID 21075794, compound

Product 1

HCID 11673425HCID 11673425, compound

Procedure

2-Ethyl-N1-isopropyl-1H-imidazo[4,5-c]quinoline-1,4-diamine was prepared in 5 steps from N′-(3-aminoquinolin-4-yl)hydrazine tert-butyl carboxylate in analogous fashion to the preparation of N1-Isopropyl-2-propyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (Example 16). Triethyl orthopropionate was used in lieu of trimethyl orthobutyrate. The material was purified by chromatography (SiO2, 20% (80:18:2 CHCl3:MeOH:NH4OH) in CHCl3) to yield an off white solid. The solid was crystallized from MeCN to yield 2-ethyl-N1-isopropyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.358 g) as light pink crystals. mp 245–247° C.; 1H NMR (500 MHz, DMSO-d6) δ 8.47 (d, J=8.1 Hz, 1H), 7.57 (d, J=8.0 Hz, 1H), 7.39 (t, J=7.5 Hz, 1H), 7.22 (t, J=7.5 Hz, 1H), 6.95 (s, 1H), 6.44 (s, 2H), 3.54–3.46 (m, 1H), 3.04–2.88 (m, 2H), 1.37 (t, J=7.1 Hz, 3H), 1.01 (d, J=5.8 Hz, 6H); 13C NMR (125 MHz, DMSO-d6) δ 155.6, 152.0, 145.0, 132.8, 126.8, 126.1, 124.1, 121.3, 120.9, 115.0, 51.2, 20.6, 19.7, 12.4; MS (APCI) m/z 270 (M+H)+; Anal. Calcd for C15H19N5: C, 66.89; H, 7.11; N, 26.00; Found: C, 66.81; H, 7.22; N, 25.95.

Workup

  1. customThe material was purified by chromatography (SiO2, 20% (80:18:2 CHCl3:MeOH:NH4OH) in CHCl3)
  2. customto yield an off white solid
  3. customThe solid was crystallized from MeCN

Sources & evidence

ORD record
ord-1d3c0316736a478c875e00a00ffd8585
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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