Water → 4-(1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carbonitrile

HRID 2205994Notes

Reaction equation

HRID 2205994 reaction equation
[CH:1]1([N:6]2[C:14]3[CH:13]=[CH:12][NH:11][C:10](=[O:15])[C:9]=3[C:8]([C:16]3[CH:17]=[C:18]([C:21]([NH2:23])=O)[S:19][CH:20]=3)=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>CC(N(C)C)=O>[CH:1]1([N:6]2[C:14]3[CH:13]=[CH:12][NH:11][C:10](=[O:15])[C:9]=3[C:8]([C:16]3[CH:17]=[C:18]([C:21]#[N:23])[S:19][CH:20]=3)=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 1370107244-(1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide

Product 1

HCID 1370107444-(1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carbonitrileYield 70.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-(1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide (25 mg) obtained in Example 13 in DMA (5 mL) was added trifluoroacetic anhydride (240 mg) under ice-cooling, and the mixture was stirred under nitrogen atmosphere at room temperature for 1 hr. To the reaction mixture was added water, the precipitate was collected by filtration, and the obtained solid was crystallized from ethyl acetate and hexane to give the title compound (16.7 mg).

Workup

  1. temperaturecooling
  2. filtrationthe precipitate was collected by filtration
  3. customthe obtained solid was crystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-b7be8deade96496191dfed38b4331b7c
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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