4-(tert-butyl)-N-(1-methyl-4-(4-methylphenyl)-3-{2-[(5-nitro-2-pyrimidinyl)oxy]ethoxy}-1H-pyrazol-5-yl)benzenesulphonamide → N-[3-{2-[(5-amino-2-pyrimidinyl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide

HRID 1062732노트

반응식

HRID 1062732 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[N:19]([CH3:20])[N:18]=[C:17]([O:21][CH2:22][CH2:23][O:24][C:25]3[N:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][N:26]=3)[C:16]=2[C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[NH2:31][C:28]1[CH:29]=[N:30][C:25]([O:24][CH2:23][CH2:22][O:21][C:17]2[C:16]([C:34]3[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=3)=[C:15]([NH:14][S:11]([C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:10][CH:9]=3)(=[O:13])=[O:12])[N:19]([CH3:20])[N:18]=2)=[N:26][CH:27]=1

참가 물질

4

반응물 1

HCID 222819704-(tert-butyl)-N-(1-methyl-4-(4-methylphenyl)-3-{2-[(5-nitro-2-pyrimidinyl)oxy]ethoxy}-1H-pyrazol-5-yl)benzenesulphonamide

생성물 1

HCID 22281919N-[3-{2-[(5-amino-2-pyrimidinyl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide수율 47.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A solution of 4-(tert-butyl)-N-(1-methyl-4-(4-methylphenyl)-3-{2-[(5-nitro-2-pyrimidinyl)oxy]ethoxy}-1H-pyrazol-5-yl)benzenesulfonamide (Example 36) (1276 mg) in ethanol (20 ml) was placed under an atmosphere of hydrogen at 50 psi for 12 hrs using palladium on carbon (5%) as catalyst. The catalyst was filtered through Celite (30 g), and washed with ethanol (3×10 ml). Concentration of the filtrate under reduced pressure afforded a yellow residue. The crude material was purified by column chromatography on silica gel (150 g), eluting with ethyl acetate:hexane (1:1), to yield the title compound as a yellow solid (569 mg).

후처리

  1. filtrationThe catalyst was filtered through Celite (30 g)
  2. washwashed with ethanol (3×10 ml)
  3. customConcentration of the filtrate under reduced pressure afforded a yellow residue
  4. customThe crude material was purified by column chromatography on silica gel (150 g)
  5. washeluting with ethyl acetate:hexane (1:1)

출처 및 근거

ORD 기록
ord-f9edf5c2e0a24b54923973a5732f9a86
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06962923B2

반응 노트

불러오는 중…