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

HRID 476186Notes

Reaction equation

HRID 476186 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.[N:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][C:42]=2[S:44](Cl)(=[O:46])=[O:45])[CH:37]=[CH:36][CH:35]=1.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:42]3[CH:41]=[CH:40][CH:39]=[C:38]4[C:43]=3[N:34]=[CH:35][CH:36]=[CH:37]4)(=[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 8471TriethylamineHCID 292208-Quinolinesulfonyl chlorideHCID 668966092-(4-(8-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile2×

Product 1

HCID 498535912-Methyl-2-(4-(8-methyl-2-oxo-3-(quinolin-8-ylsulfonyl)-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 quinoline-8-sulfonyl chloride (100 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: 32 mg (20%); 1H NMR (DMSO-d6, 300 MHz): δ 9.468 (s, 1H), 8.700-8.729 (d, 1H, J=8.7 Hz), 8.539-8.558 (m, 2H), 8.449-8.479 (d, 1H, J=9 Hz), 7.974-8.004 (d, 1H, J=9 Hz), 7.864-7.916 (t, 1H), 7.716-7.744 (d, 2H, J=8.4 Hz), 7.519-7.600 (q, 1H), 7.470-7.491 (m, 3H), 6.435 (s, 1H), 2.118 (s, 3H), 1.743 (s, 6H); MS: m/z 534 (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-4d636abf7c6e41cc94c71e574cfa7fd6
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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