(4-Aminophenoxy)benzene → 6-Fluoro-4-(4-phenoxyanilino)-1,7-naphthyridine-3-carbonitrile

HRID 276863

반응식

HRID 276863 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14].[O:15]([C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+]>CO.[Cl-].[Na+].O>[F:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][N:8]=1)[N:5]=[CH:4][C:3]([C:13]#[N:14])=[C:2]2[NH:26][C:25]1[CH:24]=[CH:23][C:22]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:28][CH:27]=1

참가 물질

6

반응물 3

HCID 8764(4-Aminophenoxy)benzeneHCID 516892Sodium BicarbonateHCID 185489604-Chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile

생성물 1

HCID 185489566-Fluoro-4-(4-phenoxyanilino)-1,7-naphthyridine-3-carbonitrile수율 69%

시약·촉매·용매 2

HCID 887Methanol용매HCID 57417360Sodium chloride; water용매

실험 절차

To 2.0 g of 4-chloro-6-fluoro-[1.7]naphthyridine-3-carbonitrile in 50 mL of methanol was added 2.2 g of 4-phenoxyaniline. After stirring the reaction under an inert atmosphere for 18 hr, the reaction mixture was poured into a mixture of brine and saturated aqueous sodium bicarbonate and the resultant crystals filtered and washed with water. The product was then recrystallized from chloroformhexanes. Drying in vacuo yielded 2.35 g (69%) of 6-fluoro-4-(4-phenoxy-phenylamino)-[1.7]naphthyridine-3-carbonitrile as yellow needles: melting point 211-213° C.; mass spectrum (m/e): M+H 356.9.

후처리

  1. customthe reaction under an inert atmosphere for 18 hr
  2. filtrationthe resultant crystals filtered
  3. washwashed with water
  4. customThe product was then recrystallized from chloroformhexanes
  5. customDrying in vacuo

출처 및 근거

ORD 기록
ord-d0aa85005d3e41988f68ffd694a1f31c
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355636B1

연결된 노트

불러오는 중…