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Diisopropylethylamine → [(2-{4-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinyl}ethyl)sulfonyl]phenylamine

HRID 855584
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HRID 855584 반응식
[C:1]1([NH:7][S:8]([CH:11]=[CH2:12])(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[CH3:22][C:23]1[S:24][C:25]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][C@H:34]([OH:42])[CH2:35][N:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)=[CH:28][C:26]=2[N:27]=1>CCO>[OH:42][C@@H:34]([CH2:33][O:32][C:29]1[CH:30]=[CH:31][C:25]2[S:24][C:23]([CH3:22])=[N:27][C:26]=2[CH:28]=1)[CH2:35][N:36]1[CH2:37][CH2:38][N:39]([CH2:12][CH2:11][S:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:10])=[O:9])[CH2:40][CH2:41]1
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 12322399N-phenylethene-1-sulfonamideHCID 29943216(2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol

생성물 1

HCID 11179355[(2-{4-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinyl}ethyl)sulfonyl]phenylamine

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
85 °C

실험 절차

To a solution of phenyl(vinylsulfonyl)amine (141 mg, 0.77 mmol) and DIEA (0.47 mL, 4.9 mmol) in EtOH (7.5 mL) was added (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazin-1-ylpropan-2-ol (470 mg, 1.5 mmol, crude). The solution was heated for 2 hours at 85° C. on a J-Kem™ block. Upon cooling, the reaction mixture was concentrated to an oil and purified via flash column chromatography (4:1 EtOAc/MeOH) to afford [(2-{4-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinyl}ethyl)sulfonyl]phenylamine.

후처리

  1. temperatureUpon cooling
  2. concentrationthe reaction mixture was concentrated to an oil
  3. custompurified via flash column chromatography (4:1 EtOAc/MeOH)

출처 및 근거

ORD 기록
ord-59da7c17812943aa921c05e1ebe0d25d
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07262198B2

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