tert-butyl 3-{[3-(3-chloro-5-cyanophenoxy)-2-oxo-4-(trifluoromethyl)pyridin-1(2H)-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate → HCID 178509917, compound

HRID 1952361Notes

Reaction equation

HRID 1952361 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:34]=[C:35]([C:37]#[N:38])[CH:36]=1)[O:5][C:6]1[C:7](=[O:33])[N:8]([CH2:16][C:17]2[C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[N:19](C(OC(C)(C)C)=O)[N:18]=2)[CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13]>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:36]=[C:35]([CH:34]=[C:4]([O:5][C:6]2[C:7](=[O:33])[N:8]([CH2:16][C:17]3[C:25]4[C:20](=[N:21][CH:22]=[CH:23][CH:24]=4)[NH:19][N:18]=3)[CH:9]=[CH:10][C:11]=2[C:12]([F:14])([F:15])[F:13])[CH:3]=1)[C:37]#[N:38]

Participants

3

Reactant 1

HCID 68508502tert-butyl 3-{[3-(3-chloro-5-cyanophenoxy)-2-oxo-4-(trifluoromethyl)pyridin-1(2H)-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

Product 1

HCID 178509917HCID 178509917, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a round bottom flask charged with tert-butyl 3-{[3-(3-chloro-5-cyanophenoxy)-2-oxo-4-(trifluoromethyl)pyridin-1(2H)-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (0.940 g, 1.72 mmol) was added TFA (50 mL). After 30 minutes, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in hot acetonitrile (500 mL), hot filtered and allowed to cool to room temperature. After 1 day, the crystallized solids were filtered to yield the title compound as a white solid. 1H NMR (DMSO-d6) δ 13.65 (s, 1H), 8.52 (d, J=4.5 Hz, 1H), 8.15 (d, J=8.1 Hz, 1H), 8.05 (d, J=7.2 Hz, 1H), 7.76-7.73 (m, 1H), 7.58-7.54 (m, 1H), 7.51-7.48 (m, 1H), 7.18 (dd, J=8.1 Hz, J=4.5 Hz, 1H), 6.63 (d, J=7.3 Hz, 1H), 5.53 (s, 2H). HRMS (M+1)=446.0626.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in hot acetonitrile (500 mL)
  3. filtrationhot filtered
  4. waitAfter 1 day
  5. filtrationthe crystallized solids were filtered

Sources & evidence

ORD record
ord-3a9b0c046dd94a80866b294b4c003b37
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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