HCID 22180884, compound → HCID 22180883, compound

HRID 2270064Notes

Reaction equation

HRID 2270064 reaction equation
[ClH:1].[NH2:2][C:3]1[C:12]2[N:13]=[C:14]([CH2:33][CH2:34][CH2:35][CH3:36])[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][S:21]([C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]=1>CO.[Pd]>[ClH:1].[NH2:2][C:3]1[C:12]2[N:13]=[C:14]([CH2:33][CH2:34][CH2:35][CH3:36])[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][S:21]([C:24]3[CH:25]=[CH:26][C:27]([NH2:30])=[CH:28][CH:29]=3)(=[O:23])=[O:22])[C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]=1

Participants

4

Reactant 1

HCID 22180884HCID 22180884, compound

Product 1

HCID 22180883HCID 22180883, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N1-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl) butyl]-4-nitro-1-benzenesulfonamide hydrochloride (0.38 g) in methanol (250 ml) was charged with a catalytic amount of 10% palladium on carbon (0.085 g). The reaction was placed under an atmosphere of hydrogen (50 psi; 3.44×105 Pa)) and shaken on a Parr apparatus for 2 hours. The reaction mixture was filtered and the solvent removed in vacuo. The solid product was recrystallized from 2-propanol to provide 0.34 g of N1-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-amino-1-benzenesulfonamide hydrochloride as an off white powder, m.p. 203.1-205.0° C. 1H NMR (300 MHz, DMSO-d6) δ 8.65 (very broad s, 2H), 8.21(d, J=8.0 Hz, 1H), 7.82 (m, 1H), 7.71 (t, J=7.7 Hz, 1H), 7.58 (t, J=7.7 Hz, 1H), 7.38 (d, J=8.7 Hz, 2H), 7.13 (t, J=5.9 Hz, 1H), 6.60 (d, J=8.7 Hz, 2H), 5.92 (broad s, 2H), 4.55 (t, J=7.6 Hz, 2H), 2.96 (t, J=7.6 Hz, 2H), 2.70 (q, J=6.4 Hz, 2H), 1.81 (m, 4H), 1.58-1.43 (m, 4H), 0.96 (t, J=7.4 Hz, 3H); IR (KBr) 3430, 3316, 3046, 2955, 2868, 2679, 1671, 1594, 1334, 1157, 1091, 851, 776, 759 cm−1; MS (EI) m/e 466.2145 (466.2151 calcd for C24H30N6O2S). Anal calcd for C24H30N6O2S*HCl: C, 57.30; H, 6.21; N, 16.71. Found: C, 57.36; H, 6.31; N, 16.21.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent removed in vacuo
  3. customThe solid product was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-34afd70331c7443da9b8a264cb4b92a0
Source dataset
uspto-grants-2001_12
Patent number
US06331539B1

Reaction notes

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