Water → 1-(4-Chloroquinolin-7-ylmethyl)-4-(6-chlorobenzo[b]thiophen-2-sulfonyl)-piperazin-2-one

HRID 1432988Notes

Reaction equation

HRID 1432988 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][C@@H:16](C)[C:15]3=[O:21])=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl:29][C:30]1[CH:31]=[CH:32][C:33]2[CH:37]=[C:36]([S:38](Cl)(=[O:40])=[O:39])[S:35][C:34]=2[CH:42]=1.O>C(#N)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:38]([C:36]4[S:35][C:34]5[CH:42]=[C:30]([Cl:29])[CH:31]=[CH:32][C:33]=5[CH:37]=4)(=[O:40])=[O:39])[CH2:16][C:15]3=[O:21])=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 151586416-Chlorobenzo[b]thiophene-2-sulfonyl chlorideHCID 69024355HCID 69024355, compound

Product 1

HCID 179852311-(4-Chloroquinolin-7-ylmethyl)-4-(6-chlorobenzo[b]thiophen-2-sulfonyl)-piperazin-2-oneYield 67.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

1-(4-chloroquinolin-7-ylmethyl)-3-(S)-methylpiperazin-2-one hydrochloride (0.49 g, 1.4 mmol), EXAMPLE 89, is treated with acetonitrile (20 mL), triethyl amine (1.2 ml, 8.4 mmol) and a solution of 6-chlorobenzo[b]thiophen-2-sulfonyl chloride (0.41 g, 1.54 mmol), EXAMPLE 1, in acetonitrile (10 mL) at 0° C. After 2 h the solution is poured into water and extracted with ethyl acetate. The organic layer is washed with water, dried over sodium sulfate and concentrated to yielded the title compound (0.45 g, 0.95 mmol). MS m/z: 506, [M+1]+; 1H NMR (CD3OD, 300 MHz) δ8.8 (d, 1H), 8.15 (d, 1H), 7.9 (d, 2H), 7.85 (s, 1H), 7.4-7.5 (m, 2H), 6.8 (s, 1H), 4.8 (s, 2H), 4.0 (s, 2H), 3.4-3.45 (m, 4H).

Workup

  1. customat 0° C
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-46a88451f2434cc58eb5edafd9e70cf9
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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