Tert-butyl 2-(3-(3-cyanophenyl)-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate → 3-(5-Piperidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile

HRID 1791364노트

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HRID 1791364 반응식
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=2)[N:15]=1)=O)(C)(C)C>C(O)=O>[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=2)[C:25]#[N:26])[N:15]=1

참가 물질

3

반응물 1

HCID 69619392Tert-butyl 2-(3-(3-cyanophenyl)-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate

생성물 1

HCID 103549563-(5-Piperidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile수율 77.4%

시약·촉매·용매 1

HCID 284Formic Acid용매

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온도
45 °C

실험 절차

2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-piperidine-1-carboxylic acid tert-butyl ester (8.1 g) was mixed with 96% formic acid (80 mL) and heated at 45° C. for 1 h. The reaction mixture was concentrated in vacuo. The residue was quenched with saturated sodium bicarbonate and extracted with dichloromethane. The organic layer was dried with sodium sulfate and concentrated again. The residue was triturated with hexanes to give 4.5 g (73.4%) of the title compounds as a white solid. 1H NMR (CDCl3), δ(ppm): 8.41 (s, 1H), 8.33 (d, 1H), 7.78 (dd, 1H), 7.61 (t, 1H), 4.15 (dd, 1H), 3.20 (m, 1H), 2.84 (m, 1H), 2.14 (m, 1H), 1.55–2.00 (m, 5H).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was quenched with saturated sodium bicarbonate
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. concentrationconcentrated again
  6. customThe residue was triturated with hexanes

출처 및 근거

ORD 기록
ord-66a50e87870749f6a6723fc9a87525a5
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074809B2

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