Carbon Tetrachloride → N-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-(6-chloro-4-(isopropylamino)pyridin-3-yl)-1,3,4-oxadiazol-2-amine

HRID 595435노트

반응식

HRID 595435 반응식
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([NH:15][NH:16][C:17](=O)[C:18]1[C:23]([NH:24][CH:25]([CH3:27])[CH3:26])=[CH:22][C:21]([Cl:28])=[N:20][CH:19]=1)=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCN(CC)CC.C(Cl)(Cl)(Cl)Cl>C(Cl)Cl>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[O:14][C:17]([C:18]2[CH:19]=[N:20][C:21]([Cl:28])=[CH:22][C:23]=2[NH:24][CH:25]([CH3:27])[CH3:26])=[N:16][N:15]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 89689674N-(3-((tert-butyldimethylsilyl)oxy)propyl)-2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinecarboxamide

생성물 1

HCID 89690916N-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-(6-chloro-4-(isopropylamino)pyridin-3-yl)-1,3,4-oxadiazol-2-amine

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
50 °C

실험 절차

N-(3-((tert-butyldimethylsilyl)oxy)propyl)-2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinecarboxamide (50) (1 g, 2.2 mmol) in DCM (40 mL) was stirred at room temperature. Added triphenyl phosphine (6 mmol, 3 equiv.), Et3N (18 mol, 8 equiv.) and CCl4 (6 mmol, 3 equiv.). The reaction mixture was heated at 50° C. for 3 h. Reaction mixture was diluted using DCM. The DCM layer was washed with water. The organic layer was collected, dried over Na2SO4, filtered and concentrated. The crude material was purified by column chromatography through silica gel and EtOAc: Pet. Ether as eluent to provide the desired compound, N-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-(6-chloro-4-(isopropylamino)pyridin-3-yl)-1,3,4-oxadiazol-2-amine. LC/MS: Acquity BEH C18 2.1×50 mm, 1.8 micron; Solvent A=0.1% TFA in water; Solvent B=0.1% TFA in ACN; gradient 0-100% B over 2 min; retention time: 1.2 min; LCMS (ES-API), m/z 426.9 (M+H).

후처리

  1. customReaction mixture
  2. additionwas diluted
  3. washThe DCM layer was washed with water
  4. customThe organic layer was collected
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by column chromatography through silica gel and EtOAc

출처 및 근거

ORD 기록
ord-9d926b3e1b3b41478315ae605a8cedf9
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242975B2

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