Acetic Acid → 6-(3-Amino-propyl)-1-(4-methoxy-phenyl)-3-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one

HRID 720441Notes

Reaction equation

HRID 720441 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:22])[N:15]([CH2:18][CH2:19][C:20]#[N:21])[CH2:16][CH2:17][C:12]=3[C:11]([C:23]([F:26])([F:25])[F:24])=[N:10]2)=[CH:5][CH:4]=1.C(O)(=O)C>CO.[Pt]=O>[NH2:21][CH2:20][CH2:19][CH2:18][N:15]1[CH2:16][CH2:17][C:12]2[C:11]([C:23]([F:26])([F:25])[F:24])=[N:10][N:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:13]=2[C:14]1=[O:22]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 100673173-[1-(4-Methoxy-phenyl)-7-oxo-3-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-propionitrile

Product 1

HCID 100675906-(3-Amino-propyl)-1-(4-methoxy-phenyl)-3-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-oneYield 85.2%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

3-[1-(4-Methoxy-phenyl)-7-oxo-3-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-propionitrile (0.050 g, 0.137 mmol) was dissolved in methanol (20 mL) in a Parr bottle. Platinum oxide (0.005 g, 10%) and acetic acid (5 mL) were added and the reaction was hydrogenated under pressure overnight, filtered over Celite®, washed with methanol, concentrated, and purified with reverse phase HPLC and freeze-drying to afford the title compound (0.043 g, 85%): 1H NMR (CDCl3) δ 8.22 (bs, 2H), 7.39 (d, j=8.8 Hz, 2H), 6.95 (d, j=8.8 Hz, 2H), 3.83 (s, 3H), 3.71 (t, j=6.8 Hz, 2H), 3.61–3.58 (m, 2H), 3.05 (t, j=6.8 Hz, 2H), 2.91 (bs, 2H), 1.99 (bs, 2H) ppm; Mass Spec 369.3(M+H)+.

Workup

  1. customwas hydrogenated under pressure overnight
  2. filtrationfiltered over Celite®
  3. washwashed with methanol
  4. concentrationconcentrated
  5. custompurified with reverse phase HPLC
  6. customfreeze-drying

Sources & evidence

ORD record
ord-eca0d4bde450468895a88516d0880897
Source dataset
uspto-grants-2006_11
Patent number
US07135469B2

Reaction notes

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