Sodium hydride → 6-[2-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamino]nicotinonitrile

HRID 626661

反応式

HRID 626661 の反応式
[H-].[Na+].[NH2:3][C:4]1[N:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=1.Cl[C:13]1[C:18]2=[CH:19][N:20]([C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:29])[N:21]=[C:17]2[CH:16]=[CH:15][N:14]=1>CN(C=O)C>[Cl:29][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([Cl:28])[C:22]=1[N:20]1[CH:19]=[C:18]2[C:13]([NH:3][C:4]3[CH:5]=[CH:6][C:7]([C:10]#[N:11])=[CH:8][N:9]=3)=[N:14][CH:15]=[CH:16][C:17]2=[N:21]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 8182602-Amino-5-cyanopyridineHCID 866970364-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

生成物 1

HCID 696717086-[2-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamino]nicotinonitrile収率 52%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (12 mg, 0.30 mmol) was added to a solution of 6-amino-3-pyridinecarbonitrile (36 mg, 0.30 mmol) in DMF (2 mL) and the resultant mixture was stirred for 5 minutes before 4-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (80 mg, 0.27 mmol) was added. The reaction vial was sealed, purged with nitrogen and irradiated in a microwave at 150° C. for 10 minutes. The reaction 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 (40% ethyl acetate in cyclohexane) to afford the title compound as a yellow solid (53 mg, 52% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.57 (d, J=0.9 Hz, 1H), 8.98 (dd, J=2.3, 0.8 Hz, 1H), 8.47 (dd, J=8.7, 2.3 Hz, 1H), 8.04 (d, J=7.3 Hz, 1H), 7.89-7.83 (m, 2H), 7.77 (dd, J=9.1, 7.2 Hz, 1H), 7.65-7.61 (m, 2H). LCMS (Method B): RT=3.05 min, m/z: 381 [M+H+].

後処理

  1. additionwas added
  2. customThe reaction
  3. customvial was sealed
  4. custompurged with nitrogen
  5. customirradiated in a microwave at 150° C. for 10 minutes
  6. temperatureThe reaction mixture was cooled
  7. custompartitioned between ethyl acetate and water
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel flash chromatography (40% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-6ff535f1486242bdb4edf8bf6b0469ec
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

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