Ethylamine → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-(ethylamino)-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 475968

反応式

HRID 475968 の反応式
Cl[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.[CH2:27]([NH2:29])[CH3:28]>C(O)C>[CH3:24][C:23]1[CH:22]=[C:21]([CH3:25])[NH:20][C:19](=[O:26])[C:18]=1[CH2:17][NH:16][C:14]([C:4]1[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=[C:2]([NH:29][CH2:27][CH3:28])[CH:3]=1)=[O:15]

参加物

4

反応物 2

HCID 6341Ethylamine2 回HCID 565974256-Chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

生成物 1

HCID 56597706N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-(ethylamino)-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a 10 mL microwave vial equipped with stir bar, septum cap and nitrogen inlet were added 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (23 mg, 0.062 mmol) and ethanol (1 mL). Added next to the stirring suspension was ethylamine (0.100 mL, 1.230 mmol) via syringe at once. The sealed reaction mixture was irradiated (microwave) at 110° C. for 40 min, followed by addition of 0.1 mL ethylamine and further irradiation for 7 hr at 130° C. After cooling to room temperature, about 50% of the volatiles were removed by a stream of nitrogen. The reaction mixture was diluted with water (20 mL) and stirred for 10 min. The mixture was then filtered and the collected solid washed with water. The solid was dried in vacuum oven at 50° C. for 18 h, to afford the title compound as 0.17 g (71%). LCMS E-S (M+H)=383.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.17 (t, J=7.07 Hz, 3H), 1.43 (d, J=6.57 Hz, 6H), 2.12 (s, 3H), 2.21 (s, 3H), 3.35-3.39 (m, 2H), 4.31 (d, J=5.05 Hz, 2H), 4.89-5.01 (m, 1H), 5.89 (s, 1H), 6.61 (s, 1H), 7.18 (t, J=5.31 Hz, 1H), 7.83 (s, 1H), 8.44 (t, J=5.05 Hz, 1H), 11.55 (br. s., 1H).

後処理

  1. customTo a 10 mL microwave vial equipped
  2. customseptum cap
  3. additionAdded next to the stirring suspension
  4. customThe sealed reaction mixture
  5. customwas irradiated (microwave) at 110° C. for 40 min
  6. customabout 50% of the volatiles were removed by a stream of nitrogen
  7. additionThe reaction mixture was diluted with water (20 mL)
  8. stirringstirred for 10 min
  9. filtrationThe mixture was then filtered
  10. washthe collected solid washed with water
  11. customThe solid was dried in vacuum oven at 50° C. for 18 h

出典と根拠

ORDレコード
ord-c80863085089426ca74ac3a287fa1d67
出典データセット
uspto-grants-2014_01
特許番号
US08637509B2

関連ノート

読み込み中…