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

HRID 475973

反応式

HRID 475973 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.C(O)C.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>O>[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]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH:3]=1)=[O:15]

参加物

5

反応物 3

HCID 702EthanolHCID 8083MorpholineHCID 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 56597867N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(4-morpholinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

To a 10 mL reaction vial containing stir bar 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 (0.060 g, 0.160 mmol), ethanol (1.5 mL), and then morpholine (0.280 mL, 3.21 mmol) via syringe at once. The contents were capped, placed into a heat block, and heated at 120° C. for 18 h and then at 135° C. for 2 hr. After cooling to room temperature, the reaction mixture was diluted with water (40 mL), adjusted to pH 6-7, and stirred for 15 min. The contents were filtered and washed with water. The product was dried in vacuum oven at 50° C. for 5 hr. The product was obtained as 57 mg (79%). LCMS E-S (M+H)=425.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44 (d, J=6.57 Hz, 6H), 2.12 (s, 3H), 2.19 (s, 3H), 3.56-3.66 (m, 4H), 3.69-3.78 (m, 4H), 4.35 (d, J=4.80 Hz, 2H), 5.00 (quin, J=6.63 Hz, 1H), 5.89 (s, 1H), 7.13 (s, 1H), 8.03 (s, 1H), 8.65 (t, J=4.93 Hz, 1H), 11.56 (br. s., 1H).

後処理

  1. customTo a 10 mL reaction
  2. additionvial containing
  3. customThe contents were capped
  4. temperatureAfter cooling to room temperature
  5. stirringstirred for 15 min
  6. filtrationThe contents were filtered
  7. washwashed with water
  8. customThe product was dried in vacuum oven at 50° C. for 5 hr
  9. customThe product was obtained as 57 mg (79%)

出典と根拠

ORDレコード
ord-b56f4d6ffe654b4b8b301a01833ae4c9
出典データセット
uspto-grants-2014_01
特許番号
US08637509B2

関連ノート

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