Methanesulfonyl chloride → 5-Chloro-2-methylpyrido[3,4-b]pyrazin-3-yl methanesulfonate

HRID 1056244

反応式

HRID 1056244 の反応式
[Cl:1][C:2]1[C:7]2=[N:8][C:9]([OH:13])=[C:10]([CH3:12])[N:11]=[C:6]2[CH:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH3:23][S:24]([O:13][C:9]1[N:8]=[C:7]2[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][C:6]2=[N:11][C:10]=1[CH3:12])(=[O:26])=[O:25]

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178432270HCID 178432270、化合物

生成物 1

HCID 897820325-Chloro-2-methylpyrido[3,4-b]pyrazin-3-yl methanesulfonate収率 64%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 5-chloro-2-methylpyrido[3,4-b]pyrazin-3-ol (1.88 g, 9.61 mmol) in DCM (30 mL) at 0° C. was treated with DIEA (3.34 mL, 19.22 mmol) followed by methanesulfonyl chloride (1.11 mL, 14.42 mmol) (Sigma Aldich). The reaction mixture was warmed to RT and stiffed for 1 h. The mixture was diluted with DCM and washed with water. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified on a silica gel column (10-35% EtOAc in Hexanes) to give 5-chloro-2-methylpyrido[3,4-b]pyrazin-3-yl methanesulfonate (1.68 g, 6.14 mmol, 64% yield) as a brown solid. MS (ESI, pos. ion) m/z: 274.0 (M+1); 1H NMR (400 MHz, CDCl3) δ ppm 8.59 (1H, d, J=5.7 Hz), 7.85 (1H, d, J=5.7 Hz), 3.83 (3H, s), 2.85 (3H, s).

後処理

  1. washwashed with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on a silica gel column (10-35% EtOAc in Hexanes)

出典と根拠

ORDレコード
ord-f8ea379ae8ac40f2b9ce836df1c8fff0
出典データセット
uspto-grants-2016_07
特許番号
US09394297B2

関連ノート

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