Trifluoroacetic acid → N-(2-(2,5-difluorophenyl)-5-methylpyridin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine

HRID 1522638Notes

Reaction equation

HRID 1522638 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]3[CH:22]=[N:23][N:24](CC4C=CC(OC)=CC=4)[C:17]=23)[C:12]([CH3:34])=[CH:11][N:10]=1.FC1C=CC(F)=CC=1C1C=C(NC2C3C(=CN(CC4C=CC(OC)=CC=4)N=3)N=CC=2)C(C)=CN=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]3[CH:22]=[N:23][NH:24][C:17]=23)[C:12]([CH3:34])=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67469557N-(2-(2,5-difluorophenyl)-5-methylpyridin-4-yl)-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridin-7-amineHCID 67470417N-(2-(2,5-difluorophenyl)-5-methylpyridin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-7-amine

Product 1

HCID 54671061N-(2-(2,5-difluorophenyl)-5-methylpyridin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

N-(2-(2,5-Difluorophenyl)-5-methylpyridin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-7-amine and N-(2-(2,5-difluorophenyl)-5-methylpyridin-4-yl)-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridin-7-amine and trifluoroacetic acid (35.0 mL) were combined and heated at 70° C. for 3 hours. The reaction was then cooled and concentrated to give a residue which was dissolved in dichloromethane (75 mL) and added with stirring to a saturated sodium bicarbonate solution (50 mL) to give a solid. The solid was collected by filtration and dissolved in ethyl acetate (500 mL) which was extracted with brine (50 mL), dried over magnesium sulfate, filtered, and concentrated to give title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.37 (3H, s) 7.09 (1H, d, J=4.80 Hz) 7.26-7.36 (2H, m) 7.50 (1H, s) 7.75 (1H, ddd, J=9.54, 6.13, 3.28 Hz) 8.24 (1H, d, J=1.26 Hz) 8.35 (1H, d, J=5.05 Hz) 8.43 (1H, s) 8.50 (1H, s) 13.03 (1H, s). MS [M+H] found 338.3.

Workup

  1. temperatureThe reaction was then cooled
  2. concentrationconcentrated
  3. customto give a residue which
  4. additionadded
  5. customto give a solid
  6. filtrationThe solid was collected by filtration
  7. dissolutiondissolved in ethyl acetate (500 mL) which
  8. extractionwas extracted with brine (50 mL)
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-5cfa114ccd6d4e30aff5e9864821765d
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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