Acetic Acid → HCID 178451827, 화합물

HRID 1749677노트

반응식

HRID 1749677 반응식
C(O)(=O)C.[NH2:5]/[C:6](/[C:24]1[CH:29]=[N:28][C:27]([NH2:30])=[C:26]([C:31]2[O:32][C:33]([C:36]([CH3:39])([CH3:38])[CH3:37])=[N:34][N:35]=2)[N:25]=1)=[N:7]\[NH:8][C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)=O>O1CCOCC1>[NH2:30][C:27]1[N:28]=[CH:29][C:24]([C:6]2[NH:7][N:8]=[C:9]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[N:5]=2)=[N:25][C:26]=1[C:31]1[O:32][C:33]([C:36]([CH3:39])([CH3:38])[CH3:37])=[N:34][N:35]=1

참가 물질

4

반응물 2

HCID 176Acetic AcidHCID 90283740tert-butyl 4-[[(Z)-[amino-[5-amino-6-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]methylidene]amino]carbamoyl]piperidine-1-carboxylate

생성물 1

HCID 178451827HCID 178451827, 화합물수율 70%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
70 °C

실험 절차

Acetic acid (200 mL) was added to dioxane (500 mL) in a 3 L fixed double jacketed vessel and the solution was heated to 70° C. under nitrogen. (Z)-tert-butyl 4-(2-(amino(5-amino-6-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)methylene)hydrazinecarbonyl)-piperidine-1-carboxylate (74.5 g, 152.80 mmol) was added portionwise to the warm mixture. After 10 minutes the temperature was increased to 100° C. (slight reflux). The reaction mixture was stirred at 100° C. for 1.5 hours (suspension) then held at 80° C. overnight (solution formed after overnight hold). The resulting solution was concentrated under reduced pressure, then diluted with toluene, evaporated to dryness, taken up with toluene and concentrated again. The residual oil was mixed with some ethyl acetate and concentrated to dryness. A solid crystallised from solution which was triturated with MTBE (200 mL) and isolated by filtration. The filter cake was washed with water and MTBE to afford tert-butyl 4-(5-(5-amino-6-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-1H-1,2,4-triazol-3-yl)piperidine-1-carboxylate (50 g, 70%) as a grey solid.

후처리

  1. temperatureAfter 10 minutes the temperature was increased to 100° C.
  2. temperature(slight reflux)
  3. waitthen held at 80° C. overnight
  4. custom(solution formed after overnight hold)
  5. concentrationThe resulting solution was concentrated under reduced pressure
  6. additiondiluted with toluene
  7. customevaporated to dryness
  8. concentrationconcentrated again
  9. additionThe residual oil was mixed with some ethyl acetate
  10. concentrationconcentrated to dryness
  11. customA solid crystallised from solution which
  12. customwas triturated with MTBE (200 mL)
  13. customisolated by filtration
  14. washThe filter cake was washed with water and MTBE

출처 및 근거

ORD 기록
ord-c47f8dcf0e6e4dc1a82c7b1fdf1b78fe
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156831B2

반응 노트

불러오는 중…