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

HRID 1429558노트

반응식

HRID 1429558 반응식
[CH3:1][C:2]1[S:6][C:5]([N:7]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[S:15][C:16]4[CH:22]=[C:21]([C:23]5[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH:24]=5)[CH:20]=[CH:19][C:17]=4[N:18]=3)[CH2:9][CH2:8]2)=[N:4][N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[S:6][C:5]([N:7]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[S:15][C:16]4[CH:22]=[C:21]([C:23]5[CH2:28][CH2:27][NH:26][CH2:25][CH:24]=5)[CH:20]=[CH:19][C:17]=4[N:18]=3)[CH2:9][CH2:8]2)=[N:4][N:3]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 67468486tert-butyl 4-(2-(1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

생성물 1

HCID 674670502-(1-(5-Methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole수율 100.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of tert-butyl 4-(2-(1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (443 mg, 0.862 mmol) in CH2Cl2 (7 mL) at rt was added TFA (1.0 mL, 13 mmol). The reaction mixture was stirred at rt overnight. The mixture was diluted with CH2Cl2 (10 mL), washed with aq. NaOH (1 N, 15 mL), then brine. The organic layer was dried (Na2SO4), filtered, and concentrated to afford 2-(1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole (357 mg, 0.863 mmol, 100% yield) as a yellow solid. LCMS (m/z)=414 (M+H)+.

후처리

  1. washwashed with aq. NaOH (1 N, 15 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b48221ac64b74735bc14c704d23f4c23
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940716B2

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