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Trifluoroacetic acid → N-(3'-fluoro-6'-methyl-2,2'-bipyridin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine

HRID 1522635
Notes
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Reaction equation

HRID 1522635 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)[CH:12]=[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=CN=2)=NC(C)=CC=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[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)[CH:12]=[CH:11][N:10]=2)=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67469529N-(3'-fluoro-6'-methyl-2,2'-bipyridin-4-yl)-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridin-7-amineHCID 67470402N-(3'-fluoro-6'-methyl-2,2'-bipyridin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-7-amine

Product 1

HCID 54670413
N-(3'-fluoro-6'-methyl-2,2'-bipyridin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

N-(3′-Fluoro-6′-methyl-2,2′-bipyridin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-7-amine and N-(3′-fluoro-6′-methyl-2,2′-bipyridin-4-yl)-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridin-7-amine and trifluoroacetic acid (20 mL) were combined and heated at 70° C. for 3 hours. The reaction mixture was then cooled, concentrated give a residue which was suspended in dichloromethane (50 mL) and added to a saturated solution of sodium bicarbonate (50 mL) with stirring. The mixture was sonicated and filtered. The solid was dried under vacuum and suspended in ethyl acetate. The solid again collected by filtration to give N-(3′-fluoro-6′-methyl-2,2′-bipyridin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine. MS [M+H] found 321.3.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. concentrationconcentrated
  3. customgive a residue which
  4. customThe mixture was sonicated
  5. filtrationfiltered
  6. customThe solid was dried under vacuum
  7. filtrationThe solid again collected by filtration

Sources & evidence

ORD record
ord-1b1bc0356e744540bdd6a5da91d36d21
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09073918B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes