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Trifluoroacetic acid → 2-(1-(5-Fluoropyrimidin-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole

HRID 1429584
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HRID 1429584 반응식
[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([O:14][C:15]3[S:16][C:17]4[CH:23]=[C:22]([C:24]5[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH:25]=5)[CH:21]=[CH:20][C:18]=4[N:19]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([O:14][C:15]3[S:16][C:17]4[CH:23]=[C:22]([C:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH:25]=5)[CH:21]=[CH:20][C:18]=4[N:19]=3)[CH2:10][CH2:9]2)=[N:4][CH:3]=1
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참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 67467120tert-butyl 4-(2-(1-(5-fluoropyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

생성물 1

HCID 674681792-(1-(5-Fluoropyrimidin-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole수율 99.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of tert-butyl 4-(2-(1-(5-fluoropyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.27 g, 2.482 mmol) in CH2Cl2 (20 mL) was added TFA (1.9 mL, 24.8 mmol). The reaction mixture was stirred at rt overnight. The reaction mixture was diluted with CH2Cl2 (20 mL) and washed sequentially with aq. NaOH (1 N, 30 mL) and brine. The organic layer was dried (Na2SO4), filtered, and concentrated to afford 2-(1-(5-fluoropyrimidin-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole (1.01 g, 2.459 mmol, 99% yield) as a pale yellow solid. LCMS (m/z)=412 (M+H)+.

후처리

  1. washwashed sequentially with aq. NaOH (1 N, 30 mL) and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1aa66c51156144a5b4c5fec5564726ee
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08940716B2

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