1,2-Dichloroethane → 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

HRID 475950

反応式

HRID 475950 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([OH:16])=O)[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl.[NH2:31][CH2:32][C:33]1[C:34](=[O:41])[NH:35][C:36]([CH3:40])=[CH:37][C:38]=1[CH3:39].CN1CCOCC1>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([NH:31][CH2:32][C:33]2[C:34](=[O:41])[NH:35][C:36]([CH3:40])=[CH:37][C:38]=2[CH3:39])=[O:16])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:12])[CH3:13])[C:6]=2[N:7]=1

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 866776226-chloro-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

6-Chloro-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (0.12 g, 0.501 mmol), 1-hydroxy-7-azabenzotriazole (0.102 g, 0.751 mmol), EDC (0.144 g, 0.751 mmol), and 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (0.123 g, 0.651 mmol) were dissolved in dimethyl sulfoxide (3.0 mL) and stirred at room temperature. Added next to the stirring contents was N-methylmorpholine (0.220 mL, 2.003 mmol) via syringe at once. After stirring at room temperature overnight, the reaction mixture was slowly added to water (75 mL) and stirred for 10 min. After sitting for 10 min. at room temperature, the contents were filtered to afford a tan solid which was washed with water and then cold 50% aq EtOH. The contents were filtered, air-dried for 10 min., and then dried under vacuum for 1 hr. The collected solid was then further dried in a vacuum oven at 45° C. for 4 hr. The title compound was collected as 0.105 g (55%). LCMS E-S (M+H)=373.9. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.49 (d, J=6.82 Hz, 6H), 2.13 (s, 3H), 2.20 (s, 3H), 4.35 (d, J=4.80 Hz, 2H), 5.07-5.20 (m, 1H), 5.89 (s, 1H), 7.66 (s, 1H), 8.39 (s, 1H), 8.91 (t, J=4.80 Hz, 1H), 11.55 (s, 1H).

後処理

  1. additionAdded next to the stirring contents
  2. stirringAfter stirring at room temperature overnight
  3. stirringstirred for 10 min
  4. filtrationthe contents were filtered
  5. customto afford a tan solid which
  6. washwas washed with water
  7. filtrationThe contents were filtered
  8. customair-dried for 10 min.
  9. customdried under vacuum for 1 hr
  10. customThe collected solid was then further dried in a vacuum oven at 45° C. for 4 hr
  11. customThe title compound was collected as 0.105 g (55%)

出典と根拠

ORDレコード
ord-fb84c52b73a3407c980323f4be75337b
出典データセット
uspto-grants-2014_01
特許番号
US08637509B2

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