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

HRID 2212956Notes

Reaction equation

HRID 2212956 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 solution obtained from 2A) is mixed with 61.25 ml (60.77 g, 0.613 mmol) of dimethylaminoacrolein and 56.28 ml (83.88 g, 0.736 mol) of trifluoroacetic acid and boiled under argon for 3 days. The solvent is then evaporated in vacuo, and the residue is added to 2 l of water and extracted three times with 1 l of ethyl acetate each time. The combined organic phases are dried over magnesium sulfate and concentrated in a rotary evaporator. Chromatography is carried out on 2.5 kg of silica gel, eluting with a toluene/toluene-ethyl acetate=4:1 gradient. Yield: 91.6 g (49.9% of theory over two stages).

Workup

  1. customThe solvent is then evaporated in vacuo
  2. additionthe residue is added to 2 l of water
  3. extractionextracted three times with 1 l of ethyl acetate each time
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. concentrationconcentrated in a rotary evaporator
  6. washeluting with a toluene/toluene-ethyl acetate=4:1 gradient

Sources & evidence

ORD record
ord-69fe3f9a36c74fe6bc4a4bbdc28675d6
Source dataset
uspto-grants-2006_09
Patent number
US07105523B2

Reaction notes

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