HCID 86596853, compound → HCID 11545549, compound

HRID 1373978Notes

Reaction equation

HRID 1373978 reaction equation
[CH:1]([NH:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][C:13]([CH:18]=[CH:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)=[CH:12][C:11]=3[N:10]=[C:9]([NH2:26])[C:8]=2[N:7]=[C:6]1[CH2:27][CH2:28][CH3:29])([CH3:3])[CH3:2]>CCO.CO.[Pd]>[CH:1]([NH:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][C:13]([CH2:18][CH2:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)=[CH:12][C:11]=3[N:10]=[C:9]([NH2:26])[C:8]=2[N:7]=[C:6]1[CH2:27][CH2:28][CH3:29])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 86596853HCID 86596853, compound

Product 1

HCID 11545549HCID 11545549, compoundYield 23.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of N1-isopropyl-2-propyl-7-(2-pyridin-3-yl-vinyl)-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.97 g, 2.5 mmol) in 15 mL of EtOH and 15 mL of MeOH was treated with palladium on carbon (0.10 g, 0.050 mmol, 5% w/w). The mixture was placed under an atmosphere of hydrogen (3.8×105 Pa) and shaken at ambient temperature. After 3 d, the reaction mixture was filtered through a pad of CELITE filter agent and rinsed with a 1:1 MeOH:EtOH until the filtrate ran clear. The filtrate was concentrated under reduced pressure to yield a light green solid. The solid was purified by chromatography (SiO2, 10–50% (80:18:2 CHCl3:MeOH:NH4OH) in CHCl3) to yield a clear oil. The oil was twice crystallized from MeCN to give N1-isopropyl-2-propyl-7-(2-pyridin-3-ylethyl)-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.224 g) as white crystals. mp 100–103° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.43 (d, J=1.6 Hz, 1H), 8.37 (dd, J=3.8, 1.6 Hz, 1H), 8.32 (d, J=8.4 Hz, 1H), 7.68–7.64 (m, 1H), 7.37 (d, J=1.5 Hz, 1H), 7.31–7.26 (m, 1H), 7.12 (dd, J=8.4, 1.7 Hz, 1H), 6.93 (d, J=1.4 Hz, 1H), 6.39 (s, 2H), 3.52–3.44 (m, 1H), 3.00 (s, 4H), 2.89 (bs, 2H), 1.91–1.79 (m, 2H), 1.04–1.00 (m, 9H); 13C NMR (125 MHz, DMSO-d6) δ 154.2, 152.0, 150.1, 147.5, 145.0, 139.6, 137.2, 136.3, 132.8, 125.4, 123.9, 123.7, 122.0, 121.1, 113.1, 51.2, 37.0, 34.1, 28.2, 21.1, 20.6, 14.3; MS (APCI) m/z 389 (M+H)+; Anal. Calcd for C23H28N6: C, 71.10; H, 7.26; N, 21.63; Found: C, 70.87; H, 7.54; N, 21.58.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washrinsed with a 1:1 MeOH
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto yield a light green solid
  6. customThe solid was purified by chromatography (SiO2, 10–50% (80:18:2 CHCl3:MeOH:NH4OH) in CHCl3)
  7. customto yield a clear oil
  8. customThe oil was twice crystallized from MeCN

Sources & evidence

ORD record
ord-f3aadaf9f1d4422b84952c9495b37c7a
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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