Bromine → HCID 178461551, 화합물

HRID 876516노트

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HRID 876516 반응식
[CH3:1][C@@H:2]1[O:7][C@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[N:17]=[C:16]3[C:12]([N:13]=[CH:14][NH:15]3)=[C:11]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:10]=2)[CH2:3]1.[Br:24]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Br:24][C:14]1[NH:15][C:16]2[C:12]([N:13]=1)=[C:11]([N:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1)[N:10]=[C:9]([N:4]1[CH2:5][C@@H:6]([CH3:8])[O:7][C@@H:2]([CH3:1])[CH2:3]1)[N:17]=2

참가 물질

5

반응물 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 178461553HCID 178461553, 화합물

생성물 1

HCID 178461551HCID 178461551, 화합물수율 34%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-((2S,6R)-2,6-dimethyl-morpholin-4-yl)-6-morpholin-4-yl-9H-purine (860 mg, 2.70 mmol) in CH2Cl2 (5 mL) was added bromine (0.04 mL, 3.24 mmol). The mixture was stirred at ambient temperature for 3 hours. Saturated sodium thiosulfate was added. The aqueous layer was extracted with dichloromethane two times. Organic layers were combined and dried over Na2SO4 and solvent was removed under reduced pressure. The crude was purified by flash column chromatography (0-70% EtOAc/Heptane gradient) to furnish product as an off-white solid (362.1 mg, 34%). LC/MS analysis using method 7, mass (ES+) m/z 399.1 1HNMR (CDCl3): 4.31 (2H, d), 4.09 (4H, brs), 3.74 (4H, m), 3.59 (2H, m), 2.51 (2H, m), 1.18 (6H, d).

후처리

  1. extractionThe aqueous layer was extracted with dichloromethane two times
  2. dry with materialdried over Na2SO4 and solvent
  3. customwas removed under reduced pressure
  4. customThe crude was purified by flash column chromatography (0-70% EtOAc/Heptane gradient)

출처 및 근거

ORD 기록
ord-a9c8ab7ec9df4d71a66454312e5dee87
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987257B2

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