Sodium cyanoborohydride → 5-Bromo-1-methyl-3-(5-(1-(oxetan-3-yl)azetidin-3-yl)pyridin-2-ylamino)pyridine-2(1H)-one

HRID 1022111ノート

反応式

HRID 1022111 の反応式
[NH:1]1[CH2:4][CH:3]([C:5]2[CH:6]=[CH:7][C:8]([NH:11][C:12]3[C:13](=[O:20])[N:14]([CH3:19])[CH:15]=[C:16]([Br:18])[CH:17]=3)=[N:9][CH:10]=2)[CH2:2]1.[O:21]1[CH2:24][C:23](=O)[CH2:22]1.[BH3-]C#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[Br:18][C:16]1[CH:17]=[C:12]([NH:11][C:8]2[CH:7]=[CH:6][C:5]([CH:3]3[CH2:4][N:1]([CH:23]4[CH2:24][O:21][CH2:22]4)[CH2:2]3)=[CH:10][N:9]=2)[C:13](=[O:20])[N:14]([CH3:19])[CH:15]=1

参加物

6

反応物 3

HCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 580437193-(5-(azetidin-3-yl)pyridin-2-ylamino)-5-bromo-1-methylpyridin-2(1H)-one

生成物 1

HCID 866845135-Bromo-1-methyl-3-(5-(1-(oxetan-3-yl)azetidin-3-yl)pyridin-2-ylamino)pyridine-2(1H)-one収率 88.2%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

A mixture of 3-(5-(azetidin-3-yl)pyridin-2-ylamino)-5-bromo-1-methylpyridin-2(1H)-one 239b (140 mg, 0.42 mmol), oxetan-3-one (91 mg, 1.26 mmol), NaBH3CN (78 mg, 1.26 mmol), and zinc chloride (171 mg, 1.26 mmol) in methanol (10 mL) was stirred at 50° C. for 2 hours. The mixture was concentrated under reduced pressure and water (5 mL) was added to the residue. It was then extracted with dichloromethane (3×10 mL). The combined organic layer was concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50:1 dichloromethane/methanol to afford 272a (145 mg, 85%). MS-ESI: [M+H]+ 390.8

後処理

  1. concentrationThe mixture was concentrated under reduced pressure and water (5 mL)
  2. additionwas added to the residue
  3. extractionIt was then extracted with dichloromethane (3×10 mL)
  4. concentrationThe combined organic layer was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography
  6. washeluting with 50:1 dichloromethane/methanol

出典と根拠

ORDレコード
ord-6a5329abe6464ab488840afff7b74a56
出典データセット
uspto-grants-2014_05
特許番号
US08716274B2

反応ノート

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