Trifluoroacetic acid → 6-Bromo-2-piperazin-1-yl-1,3-benzothiazole

HRID 1429531노트

반응식

HRID 1429531 반응식
[Br:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 67466959Tert-butyl 4-(6-bromobenzo[d]thiazol-2-yl)piperazine-1-carboxylate

생성물 1

HCID 422816756-Bromo-2-piperazin-1-yl-1,3-benzothiazole수율 99.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of tert-butyl 4-(6-bromobenzo[d]thiazol-2-yl)piperazine-1-carboxylate (300 mg, 0.753 mmol) in CH2Cl2 (6 mL) was added TFA (0.87 mL, 11.30 mmol). Upon completion of addition, the reaction mixture was stirred at rt for 3 hrs. After this time, the reaction mixture was diluted with CH2Cl2 and washed with aqueous NaOH (1 N, 5 mL) and brine (5 mL), and then dried (Na2SO4). The reaction mixture was filtered and then concentrated under reduced pressure to obtain Compound 13B as a light yellow solid (223 mg, 0.748 mmol, 99% yield). 1H NMR (500 MHz, chloroform-d) δ ppm 7.72 (s, 1H), 7.41 (s, 2H), 3.58-3.66 (m, 4H), 2.98-3.07 (m, 4H). LC/MS (m/z)=299 (M+H)+.

후처리

  1. additionUpon completion of addition
  2. washwashed with aqueous NaOH (1 N, 5 mL) and brine (5 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-71cd7336e1b3457893e199fcc44d83c6
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940716B2

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