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Dimethyl Sulfoxide → Diisopropyl Ether

HRID 1471798
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HRID 1471798 반응식
[CH3:1][S:2]([N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[CH:12]=[C:13]3[CH:19]=[C:18]([CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[O:17][C:14]3=[CH:15][N:16]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].Cl[C:27]1[S:28][C:29]([C:32]([F:35])([F:34])[F:33])=[N:30][N:31]=1.C([O-])([O-])=O.[K+].[K+].CS(C)=O>O>[CH:14]([O:17][CH:18]([CH3:20])[CH3:19])([CH3:15])[CH3:13].[CH3:1][S:2]([N:5]1[CH2:6][CH:7]=[C:8]([C:11]2[CH:12]=[C:13]3[CH:19]=[C:18]([CH:20]4[CH2:25][CH2:24][N:23]([C:27]5[S:28][C:29]([C:32]([F:35])([F:34])[F:33])=[N:30][N:31]=5)[CH2:22][CH2:21]4)[O:17][C:14]3=[CH:15][N:16]=2)[CH2:9][CH2:10]1)(=[O:3])=[O:4]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 132467892-Chloro-5-trifluoromethyl-(1,3,4)thiadiazoleHCID 866945805-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-piperidin-4-yl-furo[2,3-c]pyridine

생성물 2

HCID 7914Diisopropyl Ether
HCID 86694585
5-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-[1-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperidin-4-yl]-furo[2,3-c]pyridine

시약·촉매·용매 1

HCID 962Water용매

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온도
60 °C

실험 절차

A mixture of 5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-piperidin-4-yl-furo[2,3-c]pyridine (HCl salt, 70 mg), 2-chloro-5-trifluoromethyl-[1,3,4]thiadiazole (35 mg), K2CO3 (55 mg), and dimethyl sulfoxide (3 mL) is stirred at 60° C. overnight. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are washed with brine, dried (Na2SO4), and concentrated. The residue is triturated with methanol and then with diisopropylether to give the title compound. LC (method 1): tR=0.94 min; Mass spectrum (ESI+): m/z=514 [M+H]+.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionthe resulting mixture is extracted with ethyl acetate
  3. washThe combined extracts are washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue is triturated with methanol

출처 및 근거

ORD 기록
ord-ed1f1d48faa14d9886d38d67b650ab86
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09012456B2

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