1,2-Dichloroethane → 2,2-Dimethylpropanoyl-ethyl-6-methyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide

HRID 490905

Reaktionsgleichung

Reaktionsgleichung von HRID 490905
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH3:22])=[C:10]([C:19](O)=[O:20])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].C(Cl)CCl.C1C=CC2N(O)[N:34]=[N:33]C=2C=1.[C:37](NN)(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39]>CN(C=O)C>[CH3:39][C:38]([CH3:41])([CH3:40])[C:37]([C:5]1[C:6]2[C:7](=[N:8][C:9]([CH3:22])=[C:10]([C:19]([NH:33][NH2:34])=[O:20])[C:11]=2[NH:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:3]([CH2:1][CH3:2])[N:4]=1)=[O:42]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 5451472,2-DimethylpropanehydrazideHCID 576751871-Ethyl-6-methyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Produkt 1

HCID 866089802,2-Dimethylpropanoyl-ethyl-6-methyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazideAusbeute 79,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Intermediate 60 (0.255 g, 0.84 mmol), EDC (0.225 g, 1.17 mmol) and HOBT (0.136 g, 1.0 mmol) in DMF (5 ml) was stirred at 20° C. for 75 minutes. Pivalic acid hydrazide (0.107 g, 0.92 mmol) was added and stirring continued for 18 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between DCM and water. The organic phase was washed with aqueous sodium hydrogen carbonate then evaporated in vacuo to afford Intermediate 61 as a white solid (0.27 g).). LCMS showed MH+=403; TRET=2.13 min.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between DCM and water
  3. washThe organic phase was washed with aqueous sodium hydrogen carbonate
  4. customthen evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ca21e630afde4d4291aae7deb4001f10
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528148B2

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