Water → 5-Bromo-1-methyl-3-(5-(3-(oxetan-3-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl)pyridin-2-ylamino)pyridine-2(1H)-one

HRID 1411630노트

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HRID 1411630 반응식
[CH:1]12[N:8]([C:9]3[CH:10]=[CH:11][C:12]([NH:15][C:16]4[C:17](=[O:24])[N:18]([CH3:23])[CH:19]=[C:20]([Br:22])[CH:21]=4)=[N:13][CH:14]=3)[CH:5]([CH2:6][CH2:7]1)[CH2:4][NH:3][CH2:2]2.[O:25]1[CH2:28][C:27](=O)[CH2:26]1.[BH3-]C#N.[Na+].O>CO.[Cl-].[Zn+2].[Cl-]>[Br:22][C:20]1[CH:21]=[C:16]([NH:15][C:12]2[CH:11]=[CH:10][C:9]([N:8]3[CH:5]4[CH2:6][CH2:7][CH:1]3[CH2:2][N:3]([CH:27]3[CH2:28][O:25][CH2:26]3)[CH2:4]4)=[CH:14][N:13]=2)[C:17](=[O:24])[N:18]([CH3:23])[CH:19]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 866842683-(5-(3,8-Diazabicyclo[3.2.1]octan-8-yl)pyridin-2-ylamino)-5-bromo-1-methyl-pyridin-2(1H)-one

생성물 1

HCID 866842695-Bromo-1-methyl-3-(5-(3-(oxetan-3-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl)pyridin-2-ylamino)pyridine-2(1H)-one수율 85.7%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 887Methanol용매

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온도
50 °C

실험 절차

A mixture of 152d (676 mg, 1.7 mmol), oxetan-3-one (251 mg, 3.5 mmol), NaBH3CN (274 mg, 4.4 mmol), and zinc chloride (592 mg, 4.4 mmol) in methanol (30 mL) was stirred at 50° C. for 5 hours. water was added and the mixture was concentrated under reduced pressure. The residue was extracted with dichloromethane three times. The combined extract was concentrated under reduced pressure to afford crude 152e as a yellow solid (650 mg, 84%), which was used in the next step without further purification. MS-ESI: [M+H]+ 446.2.

후처리

  1. concentrationthe mixture was concentrated under reduced pressure
  2. extractionThe residue was extracted with dichloromethane three times
  3. extractionThe combined extract
  4. concentrationwas concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9e5a11a228824968b549c7693d675c0a
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921353B2

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