Dichloromethane → (2S)-1-(2-methylbenzothiazol-5-yloxy)-3-(4-prop-2-ynylpiperazinyl)propan-2-ol

HRID 891059

반응식

HRID 891059 반응식
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C@@H:13]([OH:21])[CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[CH:7][C:5]=2[N:6]=1.[CH2:22](Br)[C:23]#[CH:24].C(=O)([O-])[O-].[K+].[K+].ClCCl>CC(C)=O.CO>[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C@@H:13]([OH:21])[CH2:14][N:15]3[CH2:16][CH2:17][N:18]([CH2:24][C:23]#[CH:22])[CH2:19][CH2:20]3)=[CH:7][C:5]=2[N:6]=1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 58595334(2S)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol

생성물 1

HCID 58595329(2S)-1-(2-methylbenzothiazol-5-yloxy)-3-(4-prop-2-ynylpiperazinyl)propan-2-ol수율 55.7%

시약·촉매·용매 2

HCID 180Acetone용매HCID 887Methanol용매

실험 절차

To a solution of (2S)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol (800 mg, 2.6 mmol) in acetone (20 ml) was added propargyl bromide (80% solution, 0.290 ml, 2.6 mmol) and potassium carbonate (720 mg, 5.2 mmol). The solution was heated to reflux and stirred for 5 hours. Thin layer chromatography (10:1 dichloromethane:methanol) showed formation of product. The solution was cooled and filtered. The filtrate was concentrated and purified by preparative chromatography (dichloromethane:methanol) to yield (2S)-1-(2-methylbenzothiazol-5-yloxy)-3-(4-prop-2-ynylpiperazinyl)propan-2-ol (500 mg, M+1=346.2). B. Preparation of a Compound of Formula I

후처리

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. temperatureThe solution was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by preparative chromatography (dichloromethane:methanol)

출처 및 근거

ORD 기록
ord-15213026c77949888525af9651d98d57
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001909B2

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