Acetonitrile → 1-(4-Chlorocinnolin-7-ylmethyl)-4-[2-(5-chlorothiophen-2-yl)-ethenesulfonyl]-piperazin-2-one

HRID 1432995Notes

Reaction equation

HRID 1432995 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][N:14]3[CH2:19][CH2:18][NH:17][CH2:16][C:15]3=[O:20])=[CH:10][CH:11]=2)[N:6]=[N:5][CH:4]=1.C(#N)C.C(N(CC)CC)C.[Cl:31][C:32]1[S:36][C:35]([CH:37]=[CH:38][S:39](Cl)(=[O:41])=[O:40])=[CH:34][CH:33]=1>C(OCC)(=O)C>[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][N:14]3[CH2:19][CH2:18][N:17]([S:39]([CH:38]=[CH:37][C:35]4[S:36][C:32]([Cl:31])=[CH:33][CH:34]=4)(=[O:41])=[O:40])[CH2:16][C:15]3=[O:20])=[CH:10][CH:11]=2)[N:6]=[N:5][CH:4]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 544630642-(5-Chlorothiophen-2-yl)ethenesulfonyl chlorideHCID 690256761-(4-Chlorocinnolin-7-ylmethyl)-piperazin-2-one hydrochloride

Product 1

HCID 541340031-(4-Chlorocinnolin-7-ylmethyl)-4-[2-(5-chlorothiophen-2-yl)-ethenesulfonyl]-piperazin-2-oneYield 87.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-(4-chlorocinnolin-7-ylmethyl)-piperazin-2-one hydrochloride (0.14 g, 0.4 mmol), EXAMPLE 90, is treated with acetonitrile (20 mL), triethylamine (2 mL, 14 mmol) and 2-(5-chlorothiophen-2-yl)ethene-sulfonyl chloride (0.097 g, 0.4 mmol), EXAMPLE 3, at 0° C. The solution is warmed to ambient temperature over 1.5 h and diluted with ethyl acetate. The solution is washed with 10% sodium bicarbonate solution and water, dried (sodium sulfate) and concentrated to yield the title compound (0.17 g, 0.35 mmol). MS m/z: [M+H]+=483; 1H NMR (CDCl3, 300 MHz) δ9.4 (s, 1H), 8.4 (s, 1H), 8.3 (d, 1H) 7.85 (d, 1H), 7.7 (d, 1H), 7.1 (d, 1H), 6.95 (d, 1H), 6.35 (d, 1H), 4.9 (s, 2H), 4.0 (s, 2H), 3.4-3.5 (m, 4H).

Workup

  1. washThe solution is washed with 10% sodium bicarbonate solution and water
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bd4b2da81b4f4aa7af6fd8b7baf0b086
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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