Triphenylphosphine → 4-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline

HRID 40176

반응식

HRID 40176 반응식
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH:9][C:10](=O)[CH2:11][O:12][C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH3:24])=[CH:20][CH:21]=3)[N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[Si](N=[N+]=[N-])(C)C.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([CH2:11][O:12][C:13]3[C:22]4[C:17](=[CH:18][C:19]([O:23][CH3:24])=[CH:20][CH:21]=4)[N:16]=[CH:15][CH:14]=3)=[N:9][N:8]=2)[N:7]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 5462977Diethyl azodicarboxylateHCID 86630262N'-(6-chloropyridazin-3-yl)-2-(7-methoxyquinolin-4-yloxy)acetohydrazide

생성물 1

HCID 250669924-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

N′-(6-chloropyridazin-3-yl)-2-(7-methoxyquinolin-4-yloxy)acetohydrazide (2.53 g, 7.0 mmol) was suspended in tetrahydrofuran (50 mL) then added triphenylphosphine (2.8 g, 11 mmol) and trimethylsilyl azide (1.4 ml, 11 mmol). To this suspension, was added diethylazodicarboxylate (2.0 ml, 13 mmol) in rapid drops with a syringe. The mixture became clear and hot to the touch. The reaction mixture was heated at 50° C. for 30 minutes. The reaction mixture was concentrated in vacuo. The remaining oil was triturated with diethyl ether. A gel-like solid formed which was collected on a glass frit, washing with diethyl ether. The solid was then triturated with ethyl acetate, and finally acetonitrile. An amorphous solid formed which was collected on a glass frit, washing with acetonitrile. The solid was further dried under high vacuum. In addition, the ethyl acetate filtrate was concentrated in vacuo. The remaining oil was then triturated with acetonitrile. An amorphous solid formed and was collected on a glass frit, washing with acetonitrile. The solid was further dried under high vacuum affording 4-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline as a tan solid. MS (ESI, pos. ion) m/z: 342.1 (M+1).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe remaining oil was triturated with diethyl ether
  3. customA gel-like solid formed which
  4. customwas collected on a glass frit
  5. washwashing with diethyl ether
  6. customThe solid was then triturated with ethyl acetate, and finally acetonitrile
  7. customAn amorphous solid formed which
  8. customwas collected on a glass frit
  9. washwashing with acetonitrile
  10. customThe solid was further dried under high vacuum
  11. concentrationIn addition, the ethyl acetate filtrate was concentrated in vacuo
  12. customThe remaining oil was then triturated with acetonitrile
  13. customAn amorphous solid formed
  14. customwas collected on a glass frit
  15. washwashing with acetonitrile
  16. customThe solid was further dried under high vacuum

출처 및 근거

ORD 기록
ord-851298e2ada047858e95d9b75aa367ec
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524900B2

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