Water → HCID 49854940, compound

HRID 476171Notes

Reaction equation

HRID 476171 reaction equation
[Br: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.[S:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[S:39](Cl)(=[O:41])=[O:40].O>ClCCl>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([S:39]([C:35]4[S:34][CH:38]=[CH:37][CH:36]=4)(=[O:41])=[O:40])[C:13](=[O:26])[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:25])[C:22]#[N:23])=[CH:17][CH:16]=4)[C:5]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 426095694-(8-Bromo-2,3-dihydro-2-oxo-1H-imidazo(4,5-c)quinolin-1-yl)-alpha,alpha-dimethylbenzeneacetonitrile2×

Product 1

HCID 49854940HCID 49854940, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-(8-bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile (Intermediate 1, 50 mg, 0.12 mmol) and triethylamine (24.4 mg, 0.36 mmol) in dichloromethane (6 ml) was added thiophene-2-sulfonyl chloride (32.88 mg, 0.18 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: 14 mg (17.16%); 1H NMR (DMSO-d6, 300 MHz): δ 9.37 (s, 1H), 8.229-8.246 (d, 1H, J=5.1 Hz), 8.160-8.172 (d, 1H, J=3.6 Hz), 7.982-8.012 (d, 1H, J=9 Hz), 7.822-7.850 (d, 2H, J=8.4 Hz), 7.779-7.785 (d, 1H, J=1.8 Hz), 7.720-7.748 (d, 2H, J=8.4 Hz), 7.31 (t, 1H, J=4.2 Hz), 6.763-6.770 (d, 1H, J=2.1 Hz), 1.78 (s, 6H).

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-ed7c57bba8c240d1b255c6ae7c113d56
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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