Hydrazine hydrate (1:1) → 6-[({[(1,2-dimethyl-1H-imidazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine

HRID 875218노트

반응식

HRID 875218 반응식
[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([N:23]3C(=O)C4C(=CC=CC=4)C3=O)[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][N:4]=[C:3]1[CH3:34].O.NN>O1CCCC1>[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([NH2:23])[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:5][N:4]=[C:3]1[CH3:34]

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 866507522-{6-[({[(1,2-dimethyl-1H-imidazol-5-yl)(phenyl)methylene]amino}-oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione

생성물 1

HCID 866507536-[({[(1,2-dimethyl-1H-imidazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine수율 50.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-{6-[({[(1,2-dimethyl-1H-imidazol-5-yl)(phenyl)methylene]amino}-oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione (1.02 g, 2.26 mmol) in tetrahydrofuran (30 mL) was added dropwise hydrazine hydrate (0.55 mL, 11.3 mmol). After stirring at room temperature for 28 h, the reaction mixture was filtered, the insolubles washed with ethyl acetate, and the filtrate concentrated in vacuo. Purification on silica gel afforded 6-[({[(1,2-dimethyl-1H-imidazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine [370 mg, yield 43%; HPLC/MS: m/z=322 (M+H); log P(HCOOH)=0.39].

후처리

  1. filtrationthe reaction mixture was filtered
  2. washthe insolubles washed with ethyl acetate
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification on silica gel

출처 및 근거

ORD 기록
ord-7517e2328eaf43168d28e1607d083b5c
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981111B2

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