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

HRID 1022033노트

반응식

HRID 1022033 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6d720e564c8848c1b3ca3bd9efb369ea
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716274B2

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