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

HRID 1522640Notes

Reaction equation

HRID 1522640 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 mL) were combined and heated at 70° C. for 3 hours, then cooled to room temperature and stirred overnight. The reaction mixture was then concentrated in vacuo to give a residue which was dissolved in dichloromethane (75 mL) and was poured into a saturated solution of sodium bicarbonate (50 mL) to give a solid which was collected by filtration and dissolved in ethyl acetate (500 mL), washed with brine (50 mL), dried over magnesium sulfate, filtered and concentrated to give N-(2-(2,5-difluorophenyl)-5-methylpyridin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine. 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 337.3.

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customto give a residue which
  4. customto give a solid which
  5. filtrationwas collected by filtration
  6. dissolutiondissolved in ethyl acetate (500 mL)
  7. washwashed with brine (50 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-56d52bb37a1c45d7818abe478bbdd03e
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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