Trifluoroacetic acid → 3-Ethoxycarbonyl-1-(2-fluorbenzyl)-1H-pyrazolo-(3,4,5)-pyridin

HRID 351656Notes

Reaction equation

HRID 351656 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])[N:5]=[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:3]=1.CN([C:23]([CH:25]=[CH2:26])=O)C.FC(F)(F)C(O)=O>>[F:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][N:6]1[C:2]2=[N:1][CH:23]=[CH:25][CH:26]=[C:3]2[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:5]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 17587N,N-DimethylacrylamideHCID 11391384ethyl 5-amino-1-(2-fluorobenzyl)-1H-pyrazole-3-carboxylate

Product 1

HCID 111623453-Ethoxycarbonyl-1-(2-fluorbenzyl)-1H-pyrazolo-(3,4,5)-pyridin

Procedure

The above solution from Example 20A is admixed with 61.25 ml (60.77 g, 0.613 mol) of dimethylaminoacrolein and 56.28 ml (83.88 g, 0.736 mol) of trifluoroacetic acid, and the mixture is boiled under argon for 3 days. The solvent is subsequently evaporated under reduced pressure and the residue is added to 2 l of water, and the mixture is extracted three times with 1 l of ethyl acetate in each case. The combined organic phases are dried with magnesium sulphate and concentrated using a rotary evaporator. The mixture is chromatographed over 2.5 kg of silica gel and eluted using a toluene/toluene-ethyl acetate=4:1 gradient.

Workup

  1. customThe solvent is subsequently evaporated under reduced pressure
  2. additionthe residue is added to 2 l of water
  3. extractionthe mixture is extracted three times with 1 l of ethyl acetate in each case
  4. dry with materialThe combined organic phases are dried with magnesium sulphate
  5. concentrationconcentrated
  6. customa rotary evaporator
  7. customThe mixture is chromatographed over 2.5 kg of silica gel
  8. washeluted

Sources & evidence

ORD record
ord-3ee0cc362e534f078dd05af1cf3ea256
Source dataset
uspto-grants-2004_06
Patent number
US06743798B1

Reaction notes

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