Tetrahydrofuran → N-[4-chloro-2-(triazolo[4,5-b]pyridin-1-yl)phenyl]-4-[(E)-N-hydroxy-C-methylcarbonimidoyl]benzenesulfonamide

HRID 76009

반응식

HRID 76009 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[N:21]2[C:29]3[C:24](=[N:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[N:22]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=O)[CH3:2].Cl.[NH2:31][OH:32].C1COCC1>C(#N)C.O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][S:10]([C:7]2[CH:6]=[CH:5][C:4](/[C:1](=[N:31]/[OH:32])/[CH3:2])=[CH:9][CH:8]=2)(=[O:12])=[O:11])=[C:15]([N:21]2[C:29]3[C:24](=[N:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[N:22]2)[CH:16]=1

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 443297Hydroxyamine hydrochlorideHCID 573784044-acetyl-N-(4-chloro-2-[1,2,3]triazolo[4,5-b]pyridin-1-yl-phenyl)benzenesulfonamide

생성물 1

HCID 59428153N-[4-chloro-2-(triazolo[4,5-b]pyridin-1-yl)phenyl]-4-[(E)-N-hydroxy-C-methylcarbonimidoyl]benzenesulfonamide

시약·촉매·용매 2

HCID 76524Titanium tetraethoxide촉매HCID 18373917Acetonitrile--water (1/1)용매

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온도
60 °C

실험 절차

A 4 mL vial was charged with 4-acetyl-N-(4-chloro-2-[1,2,3]triazolo[4,5-b]pyridin-1-yl-phenyl)-benzenesulfonamide (synthesized according to general procedures F and G, 100 mg, 0.23 mmol), hydroxylamine hydrochloride (49 mg, 0.70 mmol), and 2 mL THF. The resultant slurry was mixed well, then titanium ethoxide (98 μL, 47 mmol) was added and the mixture heated to 60° C. overnight. The reaction mixture was subsequently diluted with ˜2 mL of acetonitrile/H2O and purified by reversed phase HPLC to afford N-(4-chloro-2-[1,2,3]triazolo[4,5-b]pyridin-1-yl-phenyl)-4-{1-[(E)-hydroxyimino]-ethyl}benzenesulfonamide: MS (ES) M+H expected 443.0, found 443.0.

후처리

  1. additionThe resultant slurry was mixed well
  2. custompurified by reversed phase HPLC

출처 및 근거

ORD 기록
ord-21578a6e5afc47588c98aebf27174ab7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835468B2

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