Trifluoroacetic acid → HCID 67469580, compound

HRID 1522577Notes

Reaction equation

HRID 1522577 reaction equation
[F:1][C:2]1[C:3]([C:9]2[CH:14]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]4[CH:22]=[N:23][N:24](CC5C=CC(OC)=CC=5)[C:17]=34)[C:12]([CH3:34])=[CH:11][N:10]=2)=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.FC1C(C2C=C(NC3C4C(=CN(CC5C=CC(OC)=CC=5)N=4)N=CC=3)C(C)=CN=2)=NC(C)=CC=1.C(O)(C(F)(F)F)=O>>[F:1][C:2]1[C:3]([C:9]2[CH:14]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]4[CH:22]=[N:23][NH:24][C:17]=34)[C:12]([CH3:34])=[CH:11][N:10]=2)=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 67469587HCID 67469587, compoundHCID 67470419HCID 67470419, compound

Product 1

HCID 67469580HCID 67469580, compoundYield 72.8%

Conditions

Temperature
70 °C

Procedure

N-(3′-Fluoro-5,6′-dimethyl-2,2′-bipyridin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-7-amine and N-(3′-fluoro-5,6′-dimethyl-2,2′-bipyridin-4-yl)-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridin-7-amine and TFA (6.2 mL) were combined and heated at 70° C. for 3 hours. The reaction mixture was cooled, concentrated, and the residue combined with dichloromethane (20 mL). To this mixture was added saturated sodium bicarbonate (20 mL) and the reaction was let stand for 10 minutes to give a solid which was collected by filtration, subsequently dissolved in EtOAc (500 mL), and washed with brine (100 mL). The organic layer was separated, dried over Na2SO4 and concentrated to give N-(3′-fluoro-5,6′-dimethyl-2,2′-bipyridin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine (0.15 g, 0.449 mmol, 72.8% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.38 (3H, s) 2.44 (3H, s) 7.04 (1H, d, J=5.05 Hz) 7.34 (1H, dd, J=8.59, 3.28 Hz) 7.63-7.71 (2H, m) 8.24 (1H, s) 8.34 (1H, d, J=5.05 Hz) 8.43 (1H, s) 8.48 (1H, s) 13.04 (1H, s). MS [M+H] found 335.2.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. additionTo this mixture was added saturated sodium bicarbonate (20 mL)
  4. customfor 10 minutes
  5. customto give a solid which
  6. filtrationwas collected by filtration
  7. dissolutionsubsequently dissolved in EtOAc (500 mL)
  8. washwashed with brine (100 mL)
  9. customThe organic layer was separated
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-fa0c61207b70439dad0da6b222c2002e
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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