Potassium Carbonate → 5-(1,4-Diazepan-1-yl)-2-pyridinyl phenyl sulfone methanesulfonic acid salt

HRID 23875

반응식

HRID 23875 반응식
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13](Cl)=[CH:12][N:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-:18].[K+].[K+].[NH:23]1[CH2:29][CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CN(C=O)C>[CH3:10][S:7]([OH:8])(=[O:9])=[O:18].[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([N:23]3[CH2:29][CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:12][N:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 68163Hexahydro-1,4-diazepineHCID 101989402-Benzenesulfonyl-5-chloropyridine

생성물 1

HCID 102877475-(1,4-Diazepan-1-yl)-2-pyridinyl phenyl sulfone methanesulfonic acid salt수율 11.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
85 °C

실험 절차

To a mixture of 5-chloro-2-pyridinyl phenyl sulfone (2.0 g, 7.9 mmol) in DMF (50 mL) was added potassium carbonate (2.5 g, 18 mmol) and homopiperazine (1.7 g, 17 mmol). The mixture was heated at 85° C. for 72 h. The mixture then was removed from heat and partitioned between water and ethyl acetate. The layers were separated and the organic layer washed twice with water (2×100 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated. Column chromatography (silica gel, 75 mL) using 5% CH3OH in CH2Cl2 with 0.7% NH4OH and conversion to the methanesulfonate salt gave 0.182 g of the title compound; IR (drift) 1570, 1304, 1240, 1223, 1207, 1196, 1178, 1145, 1112, 1059, 1052, 785, 715, 688, 645 cm−1. 1H NMR (DMSO-d6) δ2.0, 3.1, 3.2, 3.38, 3.56, 3.78, 7.26, 7.64, 7.88, 8.21, 8.67.

후처리

  1. customThe mixture then was removed
  2. temperaturefrom heat
  3. custompartitioned between water and ethyl acetate
  4. customThe layers were separated
  5. washthe organic layer washed twice with water (2×100 ml)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-57c79025038d40cb8650cc9c2598fcb7
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855709B2

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