Hydrazine hydrate (1:1) → 2-(aminomethyl)-1-(benzhydryloxy)-5-((4-methoxybenzyl)oxy)pyridin-4(1H)-one

HRID 627293노트

반응식

HRID 627293 반응식
[CH:1]([O:14][N:15]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:18](=[O:31])[CH:17]=[C:16]1[CH2:32][N:33]1C(=O)C2C(=CC=CC=2)C1=O)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(Cl)(Cl)Cl.CO>[NH2:33][CH2:32][C:16]1[N:15]([O:14][CH:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[C:18](=[O:31])[CH:17]=1

참가 물질

5

반응물 2

HCID 24654Hydrazine hydrate (1:1)3회HCID 150932422-((1-(Benzhydryloxy)-5-((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)isoindoline-1,3-dione2회

생성물 1

HCID 150932432-(aminomethyl)-1-(benzhydryloxy)-5-((4-methoxybenzyl)oxy)pyridin-4(1H)-one수율 79%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

To a solution of 2-((1-(benzhydryloxy)-5-((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)isoindoline-1,3-dione (Intermediate 292, 1.66 g, 2.90 mmol) in chloroform (20 mL) and methanol (10 mL) at room temperature was added hydrazine monohydrate (0.284 mL, 5.80 mmol). The reaction mixture was stirred overnight at room temperature. Another 1 eq of hydrazine monohydrate was added. After 3 hours still see starting material. Added another 1 eq of hydrazine monohydrate. After 2 hours the reaction mixture was filtered to remove solids. The filtrate was concentrated. The residue was triturated with MeOH and ether and the solids filtered off. This was repeated twice more. The resulting solid was triturated once with chloroform and MeOH and the solids removed by filtration. The filtrate was concentrated to afford a yellow foam (1.01 g, 79%).

후처리

  1. waitAfter 3 hours still see starting
  2. filtrationAfter 2 hours the reaction mixture was filtered
  3. customto remove solids
  4. concentrationThe filtrate was concentrated
  5. customThe residue was triturated with MeOH and ether
  6. filtrationthe solids filtered off
  7. customThe resulting solid was triturated once with chloroform and MeOH
  8. customthe solids removed by filtration
  9. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-8a25a89803e34d5997e1ab5e6575e89b
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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