HCID 117640744, 화합물 → N-(5-chloro-6-(6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)-1-(2,2-difluorobenzo [d][1,3]dioxol-5-yl)cyclopropanecarboxamide

HRID 869910노트

반응식

HRID 869910 반응식
[Cl:1][C:2]1[C:3]([C:25]2[CH:26]=[N:27][C:28]([O:31]C)=[CH:29][CH:30]=2)=[N:4][C:5]([NH:8][C:9]([C:11]2([C:14]3[CH:24]=[CH:23][C:17]4[O:18][C:19]([F:22])([F:21])[O:20][C:16]=4[CH:15]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:6][CH:7]=1>O1CCOCC1.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2([C:14]3[CH:24]=[CH:23][C:17]4[O:18][C:19]([F:22])([F:21])[O:20][C:16]=4[CH:15]=3)[CH2:12][CH2:13]2)=[O:10])=[N:4][C:3]=1[C:25]1[CH:30]=[CH:29][C:28](=[O:31])[NH:27][CH:26]=1

참가 물질

4

반응물 1

HCID 117640744HCID 117640744, 화합물

생성물 1

HCID 117640729N-(5-chloro-6-(6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)-1-(2,2-difluorobenzo [d][1,3]dioxol-5-yl)cyclopropanecarboxamide수율 22.4%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

N-(3-Chloro-6′-methoxy-2,3′-bipyridin-6-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (124 mg, 0.270 mmol) was dissolved in a mixture of 1.2 mL of 1,4-dioxane and 0.6 mL of 4M aqueous hydrochloric acid. This solution was heated at 90° C. for 5 hours. The crude reaction mixture was quenched with triethylamine and then evaporated to dryness. The crude product was then partitioned between dichloromethane and water. The organic layer was separated, dried over sodium sulfate, and then purified on 4 g of silica gel utilizing a gradient of 0-5% methanol in dichloromethane to yield N-(5-chloro-6-(6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide as a white solid (27 mg, 22%). ESI-MS m/z calc. 445.1. found 445.9 (M+1)+. Retention time 1.62 minutes.

후처리

  1. customThe crude reaction mixture
  2. customwas quenched with triethylamine
  3. customevaporated to dryness
  4. customThe crude product was then partitioned between dichloromethane and water
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. custompurified on 4 g of silica gel utilizing a gradient of 0-5% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-28bd94c26d434269a656e989206b5da2
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969386B2

반응 노트

불러오는 중…