Trifluoroacetic acid → HCID 178434436, compound

HRID 715024Notes

Reaction equation

HRID 715024 reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[C:15]([C:17]4[CH:18]=[C:19]([S:23]([N:26]([CH3:28])[CH3:27])(=[O:25])=[O:24])[CH:20]=[CH:21][CH:22]=4)[CH:16]=[C:11]3[C:10]([CH3:29])=[N:9]2)=CC=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH3:27][N:26]([CH3:28])[S:23]([C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:15]2[CH:16]=[C:11]3[C:10]([CH3:29])=[N:9][NH:8][C:12]3=[N:13][CH:14]=2)[CH:18]=1)(=[O:24])=[O:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70810921HCID 70810921, compound

Product 1

HCID 178434436HCID 178434436, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-N,N-dimethylbenzene-sulfonamide (110) (50 mg, 0.114 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 70% ethyl acetate in hexane as pale yellow solid N,N-dimethyl-3-(3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)benzenesulfonamide 111 (30 mg). MS m/z 316.9 (M+H)+.

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-2a3b8c8d3acf4a8586db0e3a92c51d38
Source dataset
uspto-grants-2015_11
Patent number
US09187473B2

Reaction notes

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