Water → HCID 49853691, compound

HRID 476193Notes

Reaction equation

HRID 476193 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.[N:34]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[C:35]=[O:36].O>ClCCl>[CH2:37]([NH:34][C:35]([N:12]1[C:6]2[CH:7]=[N:8][C:9]3[CH:10]=[CH:11][C:2]([Br:1])=[CH:3][C:4]=3[C:5]=2[N:14]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([C:22]#[N:23])([CH3:24])[CH3:25])=[CH:17][CH:16]=2)[C:13]1=[O:26])=[O:36])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76639Benzyl isocyanateHCID 426095694-(8-Bromo-2,3-dihydro-2-oxo-1H-imidazo(4,5-c)quinolin-1-yl)-alpha,alpha-dimethylbenzeneacetonitrile2×

Product 1

HCID 49853691HCID 49853691, 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 (18 mg, 0.18 mmol) in dichloromethane (6 ml) was added (isocyanatomethyl)benzene (24.57 mg, 0.18 mmol). The reaction mixture was stirred at RT for 2 hours. Then the reaction mixture was poured on to water. The 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, 1% MeOH in chloroform) to obtain the title compound. Yield: 18 mg (20%); 1H NMR (CDCl3, 300 MHz): δ 9.89 (s, 1H), 8.95 (t, 1H), 7.978-8.008 (d, 1H, J=9 Hz), 7.762-7.790 (d, 2H, J=8.4 Hz), 7.614-7.651 (dd, 1H, J=9, 1.8 Hz), 7.500-7.529 (d, 2H, J=8.7 Hz), 7.27-7.38 (m, 5H), 7.018-7.025 (d, 1H, J=2.1 Hz), 4.642-4.611 (d, 2H, J=5.7 Hz), 1.82 (s, 6H); MS: m/z 540 (M+).

Workup

  1. customThe organic layer was 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, 1% MeOH in chloroform)

Sources & evidence

ORD record
ord-43772be68e634e6e99c159685e170c52
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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