HCID 117640744、化合物 → 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 869910ノート

反応式

HRID 869910 の反応式
[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

参加物

4

反応物 1

HCID 117640744HCID 117640744、化合物

生成物 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)cyclopropanecarboxamide収率 22.4%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-28bd94c26d434269a656e989206b5da2
出典データセット
uspto-grants-2015_03
特許番号
US08969386B2

反応ノート

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