1,2-Dichloroethane → 2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-methylpyrimidine-5-carboxamide

HRID 510046Notes

Reaction equation

HRID 510046 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[C:18]([CH3:20])[C:17]([C:21]([OH:23])=O)=[CH:16][N:15]=2)=[N:6]1.C(Cl)CCl.C1C=CC2N(O)N=[N:38]C=2C=1.N>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[C:18]([CH3:20])[C:17]([C:21]([NH2:38])=[O:23])=[CH:16][N:15]=2)=[N:6]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 66613960HCID 66613960, compound

Product 1

HCID 666142742-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-methylpyrimidine-5-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under argon, 250 mg (0.688 mmol) of the compound from example 45A were initially charged in dimethylformamide (3.8 ml). Subsequently, 145 mg (0.757 mmol) of EDC and 116 mg (0.757 mmol) of HOBt were added, and finally 77 μl (1.03 mmol) of aqueous ammonia solution (25%) were added. The reaction mixture was stirred at RT overnight and then diluted with ethyl acetate. The organic phase was washed once each with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated by rotary evaporation. The residue was admixed with tert-butyl methyl ether, and the solids were filtered off and dried under high vacuum. This gave 171 mg (66% of theory) of the title compound in solid form.

Workup

  1. washThe organic phase was washed once each with water and saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation
  5. filtrationthe solids were filtered off
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-a6eda9acab1141ba8896f7fabf1a842e
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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