Isopropyl methanesulfonate → HCID 66803052、化合物

HRID 341462

反応式

HRID 341462 の反応式
[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]

参加物

6

反応物 3

HCID 13551Isopropyl methanesulfonate2 回HCID 24758Sodium hydride2 回HCID 66802888HCID 66802888、化合物2 回

生成物 1

HCID 66803052HCID 66803052、化合物収率 39%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-a35028d0569d4c7fa6cb7660c775dfc5
出典データセット
uspto-grants-2014_11
特許番号
US08895733B2

関連ノート

読み込み中…