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Water → (S)-5-bromo-3-(5-(2-ethyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-1-methylpyridin-2(1H)-one

HRID 407637
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HRID 407637 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][C@@H:18]3[CH2:23][CH3:24])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[O:25]1[CH2:28][C:27](=O)[CH2:26]1.[BH3-]C#N.[Na+].O>CO.[Cl-].[Zn+2].[Cl-]>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([CH:27]4[CH2:28][O:25][CH2:26]4)[CH2:19][C@@H:18]3[CH2:23][CH3:24])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1
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7

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HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 86683741(S)-5-Bromo-3-(5-(2-ethylpiperazin-1-yl)pyridin-2-ylamino)-1-methylpyridin-2(1H)-one

생성물 1

HCID 86683708(S)-5-bromo-3-(5-(2-ethyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-1-methylpyridin-2(1H)-one수율 68%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매
HCID 887Methanol용매

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온도
50 °C

실험 절차

A mixture of 111d (263 mg, 0.67 mmol), oxetan-3-one (96 mg, 1.34 mmol), NaBH3CN 104 mg, 1.68 mmol), and zinc chloride (227 mg, 1.68 mmol) in methanol (10 mL) was stirred at 50° C. for 5 hours. water (10 mL) was then added to the reaction. The resulting mixture was concentrated under reduced pressure. The residue was extracted with dichloromethane three times. The combined organic layer was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 50:1 dichloromethane/methanol to afford 111e (203 mg, 68%). MS: [M+H]+ 448.

후처리

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. extractionThe residue was extracted with dichloromethane three times
  3. concentrationThe combined organic layer was concentrated under reduced pressure
  4. customthe residue was purified by silica-gel column chromatography
  5. washeluting with 50:1 dichloromethane/methanol

출처 및 근거

ORD 기록
ord-7ba375219501440a9dc6db8b7b262e31
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08754077B2

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