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Pyridine → 1-(6-Chloronaphthalen-2-ylsulfonyl)-4-[6-(4-methyl-hexahydro-1,4-diazepin-1-yl)pyridazin-3-ylcarbonyl]-piperazine Hemihydrate

HRID 1372884
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HRID 1372884 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]3[N:24]=[N:25][C:26](Cl)=[CH:27][CH:28]=3)=[O:22])[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[CH3:30][N:31]1[CH2:37][CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.N1C=CC=CC=1>CS(C)=O.C(OCC)(=O)C>[OH2:13].[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]3[N:24]=[N:25][C:26]([N:34]4[CH2:35][CH2:36][CH2:37][N:31]([CH3:30])[CH2:32][CH2:33]4)=[CH:27][CH:28]=3)=[O:22])[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]3[N:24]=[N:25][C:26]([N:34]4[CH2:35][CH2:36][CH2:37][N:31]([CH3:30])[CH2:32][CH2:33]4)=[CH:27][CH:28]=3)=[O:22])[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 1049PyridineHCID 2283491-MethylhomopiperazineHCID 210726741-(6-Chloronaphthalene-2-sulfonyl)-4-(6-chloropyridazin-3-ylcarbonyl)piperazine

생성물 1

HCID 877961221-(6-Chloronaphthalen-2-ylsulfonyl)-4-[6-(4-methyl-hexahydro-1,4-diazepin-1-yl)pyridazin-3-ylcarbonyl]-piperazine Hemihydrate수율 62.9%

시약·촉매·용매 2

HCID 679
Dimethyl Sulfoxide
용매
HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A mixture of 1-(6-chloronaphthalene-2-sulfonyl)-4-(6-chloropyridazin-3-ylcarbonyl)piperazine (0.2 g, 0.443 mmol), 1-methylhexahydro-1,4-diazepine (0.166 mL, 1.33 mmol) and pyridine (0.11 mL, 1.33 mmol) in DMSO (5 mL) was heated in a sealed tube at 80° C. overnight. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (500 mL), washed with saturated sodium bicarbonate (200 mL), water (2×150 mL) and brine, and dried over sodium sulfate. After filtration and evaporation of the solvent, the residue was purified by flash chromatography over silica, eluting with 5–7% methanol/methylene chloride, to afford the title compound (0.1 g, 43%).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with saturated sodium bicarbonate (200 mL), water (2×150 mL) and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration and evaporation of the solvent
  5. customthe residue was purified by flash chromatography over silica
  6. washeluting with 5–7% methanol/methylene chloride

출처 및 근거

ORD 기록
ord-bd384395b9c442e0a2c6f565caed977e
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07160878B2

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