Trifluoroacetic acid → 5-(3-Aminoazetidin-1-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

HRID 1959412노트

반응식

HRID 1959412 반응식
C(OC([N:8]([C:16]1[C:21]([C:22]2[O:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:25][N:26]=2)=[N:20][C:19](Br)=[CH:18][N:17]=1)C(=O)OC(C)(C)C)=O)(C)(C)C.[NH:34]1[CH2:37][CH:36]([NH:38]C(=O)OC(C)(C)C)[CH2:35]1.CCN(C(C)C)C(C)C.FC(F)(F)C(O)=O>CN(C=O)C.C(OC(=O)C)C.ClCCl>[NH2:38][CH:36]1[CH2:37][N:34]([C:19]2[N:20]=[C:21]([C:22]3[O:23][C:24]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[N:25][N:26]=3)[C:16]([NH2:8])=[N:17][CH:18]=2)[CH2:35]1

참가 물질

8

반응물 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 15194053-Aminoazetidine, 3-BOC protectedHCID 59471994Tert-butyl N-[5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate

생성물 1

HCID 667454955-(3-Aminoazetidin-1-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

A mixture of tert-butyl N-tert butoxycarbonyl-5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-ylcarbamate (200 mg, 0.3858 mmol) and tert-butyl N-(azetidin-3-yl)carbamate (66.44 mg, 0.3858 mmol) and DIPEA (99.72 mg, 134.4 μL, 0.7716 mmol) in DMF (5 mL) was heated at 90° C. After this time, the reaction mixture was cooled to room temperature and diluted with ethylacetate (5 mL), washed with water (5 mL) and concentrated in vacuo to leave a solid. The solid was dissolved in dichloromethane (10 mL) and trifluoroacetic acid (1.319 g, 891.2 μL, 11.57 mmol) was added and the resulting solution stirred at room temperature for 1 hr. The reaction mixture was concentrated in vacuo to leave an oil. The oil was redissolved in dichloromethane and concentrated in vacuo to leave the product, which was used crude in the next step.

후처리

  1. temperatureAfter this time, the reaction mixture was cooled to room temperature
  2. washwashed with water (5 mL)
  3. concentrationconcentrated in vacuo
  4. customto leave a solid
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. customto leave an oil
  7. concentrationconcentrated in vacuo
  8. customto leave the product, which

출처 및 근거

ORD 기록
ord-0d5afd3381054e59a165850b0ebf19e9
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410112B2

반응 노트

불러오는 중…