Water → 2-Methyl-2-(4-(8-methyl-3-(2-methyl-5-nitrophenylsulfonyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)propanenitrile

HRID 476185

Reaction equation

HRID 476185 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:12][C:13](=[O:26])[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([CH3:25])([CH3:24])[C:22]#[N:23])=[CH:17][CH:16]=4)[C:5]=3[C:4]=2[CH:3]=1.C(N(CC)CC)C.[CH3:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][C:36]=1[S:44](Cl)(=[O:46])=[O:45].O>ClCCl>[CH3:25][C:21]([C:18]1[CH:17]=[CH:16][C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([CH3:1])[CH:11]=[CH:10][C:9]=4[N:8]=[CH:7][C:6]=3[N:12]([S:44]([C:36]3[CH:37]=[C:38]([N+:41]([O-:43])=[O:42])[CH:39]=[CH:40][C:35]=3[CH3:34])(=[O:45])=[O:46])[C:13]2=[O:26])=[CH:20][CH:19]=1)([CH3:24])[C:22]#[N:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8457o-Toluenesulfonyl chloride, 5-nitro-HCID 8471TriethylamineHCID 668966092-(4-(8-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile2×

Product 1

HCID 498535902-Methyl-2-(4-(8-methyl-3-(2-methyl-5-nitrophenylsulfonyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)propanenitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-(8-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile (Intermediate 3, 100 mg, 0.29 mmol) and triethylamine (60 mg, 0.58 mmol) in dichloromethane (6 ml) was added 2-methyl-5-nitrobenzene-1-sulfonyl chloride (103.35 mg, 0.44 mmol) at 0° C. The reaction was stirred at RT for 3 hours. The reaction mixture was poured into cold water and organic layer was separated. The aqueous layer was extracted with dichloromethane. The combined organic layer was washed with brine dried over sodium sulfate and evaporated to dryness. The crude product was purified by column chromatography (silica gel, 2% acetone in chloroform) to obtain the title compound. Yield: 20 mg (12%); 1H NMR (CDCl3, 300 MHz): δ 9.560 (s, 1H), 9.155-9.163 (d, 1H, J=2.4 Hz), 8.384-8.420 (dd, 1H, J=8.4, 2.4 Hz), 8.050-8.079 (d, 1H, J=8.7 Hz), 7.696-7.724 (d, 2H, J=8.4 Hz), 7.538-7.564 (d, 1H, J=7.8 Hz), 7.458-7.486 (d, 3H, J=8.4 Hz), 6.708 (s, 1H), 2.760 (s, 3H), 2.236 (s, 3H), 1.742 (s, 6H); MS: m/z 542 (M+).

Workup

  1. customwas separated
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe crude product was purified by column chromatography (silica gel, 2% acetone in chloroform)

Sources & evidence

ORD record
ord-f141a6de102448e19ac0589be96a27b8
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Linked notes

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