Dimethylformamide → 3-[5-[3-[(Dimethylamino)methyl]phenyl]-1,3,4-oxadiazol-2-yl]-5-(4-propan-2-ylsulfonylphenyl)pyrazin-2-amine

HRID 78637ノート

反応式

HRID 78637 の反応式
NC[C:3]1[CH:4]=[C:5]([C:9]2[O:13][C:12]([C:14]3[C:15]([NH2:32])=[N:16][CH:17]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([S:26]([CH:29]([CH3:31])[CH3:30])(=[O:28])=[O:27])=[CH:22][CH:21]=4)[N:19]=3)=[N:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1.CI.C(=O)([O-])[O-].[K+].[K+].[CH3:41][N:42]([CH:44]=O)[CH3:43]>C(OCC)(=O)C>[CH3:43][N:42]([CH2:44][C:3]1[CH:4]=[C:5]([C:9]2[O:13][C:12]([C:14]3[C:15]([NH2:32])=[N:16][CH:17]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([S:26]([CH:29]([CH3:30])[CH3:31])(=[O:27])=[O:28])=[CH:22][CH:21]=4)[N:19]=3)=[N:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1)[CH3:41]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 594716333-[5-[3-(Aminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine

生成物 1

HCID 594722773-[5-[3-[(Dimethylamino)methyl]phenyl]-1,3,4-oxadiazol-2-yl]-5-(4-propan-2-ylsulfonylphenyl)pyrazin-2-amine収率 24%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

3-[5-[3-(aminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine (12 mg, 0.02108 mmol) was added to a solution of MeI (8.976 mg, 3.937 μL, 0.06324 mmol) and potassium carbonate (8.740 mg, 0.06324 mmol) in DMF (2 mL). The resulting mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate (3 mL) and washed successively with water (1×5 mL) and brine (1×5 mL). The organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. Product fractions were combined and lypholised to give the product as a yellow solid (3.0 mg, 24% yield); 1H NMR (400 MHz, MeOD) d 1.35-1.4 (m, 6H), 2.95 (s, 6H), 4.65 (s, 2H), 7.8-7.85 (m, 2H), 8.05-8.1 (m, 2H), 8.4-8.5 (m, 4H) and 9.95 (s, 1H) ppm; MS (ES+) 479.3

後処理

  1. washwashed successively with water (1×5 mL) and brine (1×5 mL)
  2. dry with materialThe organic extracts were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]

出典と根拠

ORDレコード
ord-9d7a1f4e61844efbbc9b5ee3af99e166
出典データセット
uspto-grants-2014_09
特許番号
US08841308B2

反応ノート

読み込み中…