Trifluoroacetic acid → HCID 178434438, compound

HRID 715023Notes

Reaction equation

HRID 715023 reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[C:15]([C:17]4[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=4)[CH:16]=[C:11]3[C:10]([CH3:23])=[N:9]2)=CC=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH3:23][C:10]1[C:11]2[C:12](=[N:13][CH:14]=[C:15]([C:17]3[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=3)[CH:16]=2)[NH:8][N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68388554HCID 68388554, compound

Product 1

HCID 178434438HCID 178434438, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(4-methoxybenzyl)-3-methyl-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-b]pyridine (107) (60 mg, 0.179 mmol) dissolved in chloroform (10 mL) was added trifluoroacetic acid (5 mL) and the reaction mixture was heated at 50° C. for 12 h. After completion of the reaction the solvents were removed and diluted with cold water, pH was adjusted to 8 and the aqueous phase extracted with chloroform two times. The organic layer was washed with brine solution and dried over sodium sulphate and the solvents were removed. The crude was passed through 100-200 mesh silica gel eluting the compound at 80% ethyl acetate in hexane as pale yellow solid 3-methyl-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-b]pyridine 108 (30 mg).

Workup

  1. customAfter completion of the reaction the solvents
  2. customwere removed
  3. additiondiluted with cold water, pH
  4. extractionthe aqueous phase extracted with chloroform two times
  5. washThe organic layer was washed with brine solution
  6. dry with materialdried over sodium sulphate
  7. customthe solvents were removed

Sources & evidence

ORD record
ord-e3c8125b48e6423ebcde52c4fb1769a9
Source dataset
uspto-grants-2015_11
Patent number
US09187473B2

Reaction notes

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