Triethylamine → 2-chloro-N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-5,6-dimethyl-3-nitropyridin-4-amine

HRID 606088노트

반응식

HRID 606088 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](Cl)=[N:9][OH:10])=[CH:4][CH:3]=1.[Cl:12][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH:22][CH2:23][C:24]#[CH:25])[C:16]([CH3:26])=[C:15]([CH3:27])[N:14]=1.C(N(CC)CC)C>ClCCl>[Cl:12][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH:22][CH2:23][C:24]2[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:25]=2)[C:16]([CH3:26])=[C:15]([CH3:27])[N:14]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27563164-fluoro-N-hydroxybenzenecarboximidoyl chlorideHCID 862476282-chloro-5,6-dimethyl-3-nitro-N-prop-2-ynylpyridin-4-amine

생성물 1

HCID 866168882-chloro-N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-5,6-dimethyl-3-nitropyridin-4-amine수율 76.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
40 °C

실험 절차

Under a nitrogen atmosphere, 4-fluoro-N-hydroxybenzenecarboximidoyl chloride (52.0 g, 225 mmol), prepared as described in Parts A through C of Example 11, was added to a solution of 2-chloro-5,6-dimethyl-3-nitro-N-prop-2-ynylpyridin-4-amine (26.92 g, 112.3 mmol) in anhydrous dichloromethane (1 L) at room temperature. Triethylamine (25 g, 250 mmol) was added; a precipitate formed. The resulting mixture was heated at 40° C. under nitrogen for 16 hours, diluted with dichloromethane, washed sequentially with aqueous potassium carbonate, water, and brine; dried over sodium sulfate; filtered; and concentrated under reduced pressure to a suspension. The suspension was filtered to isolate a yellow solid, which was washed with diethyl ether and dried under vacuum to provide 32.45 g of 2-chloro-N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-5,6-dimethyl-3-nitropyridin-4-amine.

후처리

  1. customa precipitate formed
  2. washwashed sequentially with aqueous potassium carbonate, water, and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationand concentrated under reduced pressure to a suspension
  6. filtrationThe suspension was filtered
  7. customto isolate a yellow solid, which
  8. washwas washed with diethyl ether
  9. customdried under vacuum

출처 및 근거

ORD 기록
ord-c73055667db649d89f8bf3b3c68b9982
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915281B2

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