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Triphenylphosphine → N-(4-(3-(4-chlorobenzyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)methanesulfonamide

HRID 406424
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HRID 406424 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][NH:12][C:13]2[N:18]=[N:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=O)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N([Si](C)(C)C)=[N+]=[N-].N(C(OCC)=O)=NC(OCC)=O>ClCCl.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[N:18]3[N:17]=[C:16]([C:19]4[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=4)[CH:15]=[CH:14][C:13]3=[N:12][N:11]=2)=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66849890N-(4-(6-(2-(2-(4-chlorophenyl)acetyl)hydrazinyl)pyridazin-3-yl)phenyl)methanesulfonamide

생성물 1

HCID 66849693N-(4-(3-(4-chlorobenzyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)methanesulfonamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a round bottom flask was added N-(4-(6-(2-(2-(4-chlorophenyl)acetyl)hydrazinyl)pyridazin-3-yl)phenyl)methanesulfonamide (0.928 mmole), triphenylphosphine (3.25 mmole), azidotrimethylsilane (3.25 mmole), diethyl azodicarboxylate (4.18 mmole), and THF (13 mL). The resulting mixture was stirred at room temperature for 22 hours. The reaction mixture was diluted with dichloromethane and washed with saturated NaHCO3 and brine. The organic extract was dried over Na2SO4 and evaporated in vacuo. The crude product was washed with dichloromethane and methanol. The yellow solid was further purified by recrystallization with DMF and water to yield N-(4-(3-(4-chlorobenzyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)methanesulfonamide.

후처리

  1. washwashed with saturated NaHCO3 and brine
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. customevaporated in vacuo
  5. washThe crude product was washed with dichloromethane and methanol
  6. customThe yellow solid was further purified by recrystallization with DMF and water

출처 및 근거

ORD 기록
ord-2fced20407514264a633032760252a01
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08754103B2

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