Isopropyl methanesulfonate → HCID 66803052, 화합물

HRID 341462

반응식

HRID 341462 반응식
[H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]([N:10]([CH3:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]=[C:6]([C:18]2[N:22]=[C:21]([N:23]3[CH2:26][CH:25]([OH:27])[CH2:24]3)[O:20][N:19]=2)[N:5]=1.CS(O[CH:33]([CH3:35])[CH3:34])(=O)=O>CN(C=O)C.CCOC(C)=O>[CH:33]([O:27][CH:25]1[CH2:24][N:23]([C:21]2[O:20][N:19]=[C:18]([C:6]3[N:7]=[C:8]([N:10]([CH3:17])[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:9]=[C:4]([NH2:3])[N:5]=3)[N:22]=2)[CH2:26]1)([CH3:35])[CH3:34]

참가 물질

6

반응물 3

HCID 13551Isopropyl methanesulfonate2회HCID 24758Sodium hydride2회HCID 66802888HCID 66802888, 화합물2회

생성물 1

HCID 66803052HCID 66803052, 화합물수율 39%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

Sodium hydride (60% dispersion in mineral oil, 9 mg, 0.22 mmol) was added to a solution of 1-{3-[4-amino-6-(methyl-phenyl-amino)-[1,3,5]triazin-2-yl]-[1,2,4]oxadiazol-5-yl}-azetidin-3-ol (Intermediate 166, 50 mg, 0.147 mol) in anhydrous DMF (0.5 mL) at 0 C under nitrogen and the mixture was stirred for 10 min. A solution of propan-2-yl methanesulfonate (26.7 μL, 0.221 mmol) in anhydrous DMF (0.5 mL) was then added and the mixture was stirred at room temperature for 18 h. Further sodium hydride (60% dispersion in mineral oil, 9 mg, 0.22 mmol) and propan-2-yl methanesulfonate (26.7 μL, 0.221 mmol) were then added and the mixture was stirred at room temperature for 4 h. The mixture was diluted with EtOAc (10 mL) then washed with saturated aq. sodium carbonate (4×5 mL), brine (5 mL) and evaporated under vacuum. The crude residue was purified by flash chromatography (0-2% (7M ammonia in MeOH) in DCM) to afford the title compound as a light yellow glass (22 mg, 39%).

후처리

  1. stirringthe mixture was stirred at room temperature for 18 h
  2. stirringthe mixture was stirred at room temperature for 4 h
  3. washthen washed with saturated aq. sodium carbonate (4×5 mL), brine (5 mL)
  4. customevaporated under vacuum
  5. customThe crude residue was purified by flash chromatography (0-2% (7M ammonia in MeOH) in DCM)

출처 및 근거

ORD 기록
ord-a35028d0569d4c7fa6cb7660c775dfc5
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895733B2

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