Formaldehyde → 5-Bromo-1-methyl-3-(5-(1-methylazetidin-3-yl)pyridin-2-ylamino)pyridine-2(1H)-one

HRID 592964ノート

反応式

HRID 592964 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.C=O.[BH3-][C:24]#N.[Na+].C(OCC)C>CO.[Cl-].[Zn+2].[Cl-].O>[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]([CH3:24])[CH2:2]3)=[CH:10][N:9]=2)[C:13](=[O:20])[N:14]([CH3:19])[CH:15]=1

参加物

8

反応物 4

HCID 712FormaldehydeHCID 3283Diethyl EtherHCID 5003444Sodium cyanoborohydrideHCID 580437193-(5-(azetidin-3-yl)pyridin-2-ylamino)-5-bromo-1-methylpyridin-2(1H)-one

生成物 1

HCID 580440835-Bromo-1-methyl-3-(5-(1-methylazetidin-3-yl)pyridin-2-ylamino)pyridine-2(1H)-one収率 83%

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A mixture of 239b (469 mg, 1.4 mmol), 37% aqueous formaldehyde (4.0 g, 50 mmol), NaBH3CN (261 mg, 4.2 mmol), and 1M zinc chloride in ethoxyethane (4 mL, 4.2 mmol) in methanol (40 mL) was stirred at room temperature for 2 hours. The mixture was added to water (20 mL) and concentrated under reduced pressure. The residue was extracted with dichloromethane (3×50 mL). The combined organic layer was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 10:1 methylene chloride/methanol to afford 239c as a yellow solid (300 mg, 83%). MS-ESI: [M+H]+ 349.

後処理

  1. concentrationconcentrated under reduced pressure
  2. extractionThe residue was extracted with dichloromethane (3×50 mL)
  3. concentrationThe combined organic layer was concentrated under reduced pressure
  4. customthe residue was purified by silica-gel column chromatography
  5. washeluting with 10:1 methylene chloride/methanol

出典と根拠

ORDレコード
ord-f81adc3649dc4ce0be7b7cba437ef97f
出典データセット
uspto-grants-2016_01
特許番号
US09238655B2

反応ノート

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