Hydrochloric Acid → HCID 67083316, compound

HRID 1892249Notes

Reaction equation

HRID 1892249 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([C:10]#[N:11])[N:7]=[C:6]2[C:12]([CH3:16])=[N:13][N:14]([CH3:15])[C:5]=12)([CH3:3])[CH3:2].C1COCC1.Cl>CCO.[Pd]>[CH:1]([C:4]1[CH:9]=[C:8]([CH2:10][NH2:11])[N:7]=[C:6]2[C:12]([CH3:16])=[N:13][N:14]([CH3:15])[C:5]=12)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 68161630HCID 68161630, compound

Product 1

HCID 67083316HCID 67083316, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-Isopropyl-1,3-dimethyl-1H-pyrazolo[4,3-b]pyridine-5-carbonitrile (from the previous step, 91.05 g, 5.15 mmol) was dissolved in EtOH:THF:conc.HCl (25 mL:10 mL:1.5 mL). 400 mg of 10% Pd/C was added and the reaction mixture was stirred under hydrogen balloon overnight. The catalyst was filtered out and the filtrate was concentrated under reduced pressure to afford the title compound as a white solid. Spectroscopic data: 1H-NMR (300 MHz, CD3OD): δ ppm 1.41 (d, J=6.74 Hz, 6 H), 2.56 (s, 3 H), 3.77 (hept, J=6.74 Hz, 1 H), 4.02 (s, 2 H), 4.21 (s, 3 H), 7.36 (s, 1 H).

Workup

  1. filtrationThe catalyst was filtered out
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9a2df8c36fe3420fa990af4539173f6c
Source dataset
uspto-grants-2013_08
Patent number
US08507682B2

Reaction notes

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