Hydrazine hydrate (1:1) → 3-Amino-2-[4-(5-bromo-3-methylpyrid-2-yl)-butylamino]-5-(pyrid-3-ylmethyl)pyridine

HRID 34916

반응식

HRID 34916 반응식
O.NN.[Br:4][C:5]1[CH:6]=[C:7]([CH3:32])[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[C:21]([N+:22]([O-])=O)=[CH:20][C:19]([CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:18][N:17]=2)=[N:9][CH:10]=1>CO.[Ni]>[NH2:22][C:21]1[C:16]([NH:15][CH2:14][CH2:13][CH2:12][CH2:11][C:8]2[C:7]([CH3:32])=[CH:6][C:5]([Br:4])=[CH:10][N:9]=2)=[N:17][CH:18]=[C:19]([CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH:20]=1

참가 물질

5

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 198517932-[4-(5-Bromo-3-methylpyrid-2-yl)butylamino]-3-nitro-5-(pyrid-3-ylmethyl)pyridine

생성물 1

HCID 198517893-Amino-2-[4-(5-bromo-3-methylpyrid-2-yl)-butylamino]-5-(pyrid-3-ylmethyl)pyridine수율 62.6%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매2회

실험 절차

Hydrazine hydrate (5 ml) in methanol (25 ml) was added with stirring over 20 minutes to a cooled (10° C.) solution of 2-[4-(5-bromo-3-methylpyrid-2-yl)butylamino]-3-nitro-5-(pyrid-3-ylmethyl)pyridine (4.75 g) in methanol (250 ml) containing Raney Nickel (ca. 3 g). The solution was stirred for a further 30 minutes, the catalyst was removed by filtration and the filtrate was concentrated to dryness in vacuo. The residue was chromatographed on silica eluted with 5% v/v methanol in chloroform and then recrystallized from acetonitrile to give the tile compound (2.78 g), m.p. 85°-87° C.

후처리

  1. stirringThe solution was stirred for a further 30 minutes
  2. customthe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated to dryness in vacuo
  4. customThe residue was chromatographed on silica
  5. washeluted with 5% v/v methanol in chloroform
  6. customrecrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-1b8aae2df5184c04a17fff473013080f
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04764519

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