Water → 6-Chloro-2-methyl-4-(5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)pyridazin-3(2H)-one

HRID 1919125노트

반응식

HRID 1919125 반응식
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[CH:14][N:13]=2)[C:6](=[O:10])[N:7]([CH3:9])[N:8]=1.[O:24]1[CH2:27][C:26](=O)[CH2:25]1.[BH3-]C#N.[Na+].O>CO.[Cl-].[Zn+2].[Cl-]>[Cl:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][N:21]([CH:26]4[CH2:27][O:24][CH2:25]4)[CH2:20][CH2:19]3)=[CH:14][N:13]=2)[C:6](=[O:10])[N:7]([CH3:9])[N:8]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 670162986-Chloro-2-methyl-4-(5-(piperazin-1-yl)pyridin-2-ylamino)pyridazin-3(2H)-one Hydrochloride

생성물 1

HCID 580440166-Chloro-2-methyl-4-(5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)pyridazin-3(2H)-one수율 50%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 887Methanol용매

실험 절차

A mixture of 328b (1.2 g, 3.5 mmol), oxetan-3-one (0.5 g, 7.0 mmol), NaBH3CN (0.44 g, 7.0 mmol) and zinc chloride (0.93 g, 7.0 mmol) in methanol (125 ml) was stirred at 50 degree for 3.5 hours. The mixture was added to water and extracted with methylene chloride. The organic layers were combined and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 25:1 methylene chloride/methanol to give 328c (0.63 g, 50%). MS: [M+H]+ 377.

후처리

  1. extractionextracted with methylene chloride
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography
  4. washeluting with 25:1 methylene chloride/methanol

출처 및 근거

ORD 기록
ord-0ceb0a88622049e19c13c7e32a101d63
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618107B2

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