Triethylamine → 1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1522534

Reaktionsgleichung

Reaktionsgleichung von HRID 1522534
Cl[C:2]1[CH:3]=[C:4]([C:14]([OH:16])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.CCN(CC)CC>C(O)C>[CH:11]([N:8]1[C:6]2[N:7]=[CH:2][CH:3]=[C:4]([C:14]([OH:16])=[O:15])[C:5]=2[CH:10]=[N:9]1)([CH3:13])[CH3:12]

Komponenten

4

Edukt 2

HCID 8471TriethylamineHCID 866776226-chloro-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Produkt 1

HCID 682953131-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a 100 mL round bottom flask was charged 10% Pd/C(degussa) (0.213 g, 0.100 mmol), under N2 followed by addition of ca. 5 mL EtOH. The slurry was stirred followed by addition of 6-chloro-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (0.48 g, 2.003 mmol) and ethanol (22 mL). Next added Et3N (0.837 mL, 6.01 mmol) and stirred for 5 min under nitrogen. The contents were then stirred under an atmosphere of hydrogen (1 atm) for 6 h at RT. The vessel was then flushed with nitrogen and the contents diluted with DCM (10 mL) and a small amount of celite. The contents were stirred for 10 min., filtered through analytical grade celite and washed with 10% MeOH/DCM, EtOH, then DCM. The filtrate was concentrated in vacuo to a residue and dried on hi-vacuum overnight. The solid was treated with water and adjusted to pH 3 with 1M HCl. The contents were filtered, air-dried and then dried in hi-vacuum oven at 45° C. for 18 h. The title compound was collected as 0.326 g (78%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.52 (d, J=6.82 Hz, 6 H) 5.28 (quin, J=6.69 Hz, 1 H) 7.70 (d, J=4.55 Hz, 1 H) 8.39 (s, 1 H) 8.73 (d, J=4.55 Hz, 1 H) 13.91 (br. s., 1 H). LCMS(ES) [M+H]+ 205.9

Aufarbeitung

  1. stirringstirred for 5 min under nitrogen
  2. stirringThe contents were then stirred under an atmosphere of hydrogen (1 atm) for 6 h at RT
  3. customThe vessel was then flushed with nitrogen
  4. additionthe contents diluted with DCM (10 mL)
  5. stirringThe contents were stirred for 10 min.
  6. filtrationfiltered through analytical grade celite
  7. washwashed with 10% MeOH/DCM, EtOH
  8. concentrationThe filtrate was concentrated in vacuo to a residue
  9. customdried on hi-vacuum overnight
  10. additionThe solid was treated with water
  11. filtrationThe contents were filtered
  12. customair-dried
  13. customdried in hi-vacuum oven at 45° C. for 18 h
  14. customThe title compound was collected as 0.326 g (78%)

Quellen und Nachweise

ORD-Eintrag
ord-b123d1467b6742678e74e85d075d1791
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073924B2

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