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

HRID 346527Notes

Reaction equation

HRID 346527 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 Example 1A is mixed 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 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 with magnesium sulphate 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 with magnesium sulphate
  5. concentrationconcentrated in a rotary evaporator
  6. washeluting with a toluene/toluene-ethyl acetate=4:1 gradient

Sources & evidence

ORD record
ord-d432df4fc84c4c018f80e8b02c08144e
Source dataset
uspto-grants-2007_02
Patent number
US07173037B2

Reaction notes

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