Water → 2-(4-(8-Bromo-2-oxo-3-(phenylsulfonyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile

HRID 476169Notes

Reaction equation

HRID 476169 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.[C:34]1([S:40](Cl)(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O>ClCCl>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([S:40]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)(=[O:42])=[O:41])[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 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 426095694-(8-Bromo-2,3-dihydro-2-oxo-1H-imidazo(4,5-c)quinolin-1-yl)-alpha,alpha-dimethylbenzeneacetonitrile2×

Product 1

HCID 498549382-(4-(8-Bromo-2-oxo-3-(phenylsulfonyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile

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 benzenesulfonyl chloride (31.8 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 organic layer was dried on sodium sulfate and evaporated to dryness to obtain the title compound. Yield: 20 mg (29.7%); 1H NMR (CDCl3, 300 MHz): δ 9.59 (s, 1H), 8.198-8.227 (d, 2H, J=8.7 Hz), 7.958-7.989 (d, 1H, J=8.7 Hz), 7.70-7.723 (d, 2H, J=6.9 Hz), 7.57-7.69 (m, 4H), 7.40-7.436 (d, 2H, J=8.7 Hz), 6.97-6.981 (d, 1H, J=2.1 Hz), 1.79 (s, 6H).

Workup

  1. customwas separated
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. customThe organic layer was dried on sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-804723c1e42140ff9a3091805edd409d
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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