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

HRID 475969

반응식

HRID 475969 반응식
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>[Pd].C1COCC1>[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]=[CH:2][CH:3]=1)=[O:15]

참가 물질

5

반응물 2

HCID 702EthanolHCID 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

생성물 1

HCID 56597295N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a 50 mL round bottom flask fitted with a 3-way inlet was placed 10% Pd/C (0.071 g, 0.033 mmol) followed by degassing with N2, and then addition of 2 mL ethanol. Added next to the stirring slurry was 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 (0.25 g, 0.669 mmol). Additional ethanol (8 mL) and THF (10 mL) were added with slight warming to facilitate dissolution. The stirring contents were allowed to cool (15 min.) then fitted with a balloon of H2 and allowed to stir at room temperature overnight. The contents were then purged with N2. The mixture was then diluted with 10% MeOH/DCM (20 mL), stirred for 10 min., and filtered through Celite. The filtrate was concentrated in vacuo and the crude solid was triturated with ethanol. After filtration and washing the collected solid with additional ethanol (cold), the solid was air-dried for 15 min, then in vacuum oven at 40° C. overnight. The final product was collected as 185 mg (80%). LCMS E-S (M+H)=340.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50 (d, J=6.82 Hz, 6H), 2.13 (s, 3H), 2.22 (s, 3H), 4.37 (d, J=4.80 Hz, 2H), 5.18-5.31 (m, 1H), 5.89 (s, 1H), 7.54 (d, J=4.80 Hz, 1H), 8.36 (s, 1H), 8.63 (d, J=4.55 Hz, 1H), 8.82 (t, J=4.93 Hz, 1H), 11.56 (s, 1H).

후처리

  1. customTo a 50 mL round bottom flask fitted with a 3-way inlet
  2. customby degassing with N2
  3. additionaddition of 2 mL ethanol
  4. additionAdded next to the stirring slurry
  5. temperaturewith slight warming
  6. dissolutiondissolution
  7. temperatureto cool (15 min.)
  8. customthen fitted with a balloon of H2
  9. customThe contents were then purged with N2
  10. additionThe mixture was then diluted with 10% MeOH/DCM (20 mL)
  11. stirringstirred for 10 min.
  12. filtrationfiltered through Celite
  13. concentrationThe filtrate was concentrated in vacuo
  14. customthe crude solid was triturated with ethanol
  15. filtrationAfter filtration
  16. washwashing the collected solid with additional ethanol (cold)
  17. customthe solid was air-dried for 15 min
  18. customat 40° C.
  19. customovernight
  20. customThe final product was collected as 185 mg (80%)

출처 및 근거

ORD 기록
ord-e87ef3775cea46d48b8f7e64a0067aa8
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637509B2

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