反応式
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[C:14]3=[CH:15][N:16]([C:18]4[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=4[Cl:25])[N:17]=[C:13]3[CH:12]=[CH:11][N:10]=2)[CH:3]=1.[CH3:26][NH2:27]>CN1C(=O)CCC1>[Cl:24][C:23]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:25])[C:18]=1[N:16]1[CH:15]=[C:14]2[C:9]([NH:8][C:4]3[CH:3]=[C:2]([NH:27][CH3:26])[N:7]=[CH:6][N:5]=3)=[N:10][CH:11]=[CH:12][C:13]2=[N:17]1参加物
実験手順
A solution of (6-chloropyrimidin-4-yl)-[2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-4-yl]amine (80 mg, 0.20 mmol) and methylamine (2M in THF, 300 μL, 0.60 mmol) in NMP (2.0 mL) was sealed in a microwave vial, purged with nitrogen and irradiated at 160° C. for 30 minutes in the microwave. Further methylamine (300 μL, 0.20 mmol) was added and the reaction mixture was irradiated at 170° C. for 30 minutes. The resultant mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (4-5% methanol in DCM) to afford the title compound as a white solid (35.0 mg, 45% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.03 (br s, 1H), 9.14 (s, 1H), 8.21 (s, 1H), 7.91 (d, J=6.3 Hz, 1H), 7.80 (d, J=8.1 Hz, 2H), 7.70 (dd, J=9.0, 7.4 Hz, 1H), 7.23 (br s, 1H), 7.13 (d, J=6.4 Hz, 1H), 2.81 (d, J=4.7 Hz, 3H). LCMS (Method B): RT=2.99 min, m/z: 386 [M+H+].
後処理
- custompurged with nitrogen
- customirradiated at 160° C. for 30 minutes in the microwave
- customthe reaction mixture was irradiated at 170° C. for 30 minutes
- custompartitioned between ethyl acetate and water
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel flash chromatography (4-5% methanol in DCM)
出典と根拠
- ORDレコード
- ord-b973125bd98e46ff900de4068e40b2e0
- 出典データセット
- uspto-grants-2016_04
- 特許番号
- US09309240B2
関連ノート
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