Pyridine → HCID 178470411, compound

HRID 2115262Notes

Reaction equation

HRID 2115262 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.F[C:12](F)(F)[C:13]([OH:15])=[O:14].CC1C(C)=CC2NC(C3[NH:27][N:28]=[C:29]4[C:34]=3[CH2:33][CH2:32][NH:31][CH2:30]4)=NC=2C=1.N1C=CC=[CH:40][CH:39]=1>>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:31]2[CH2:32][CH2:33][C:34]3=[C:12]([C:13]([O:15][CH2:39][CH3:40])=[O:14])[NH:27][N:28]=[C:29]3[CH2:30]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 3

HCID 1049PyridineHCID 783082-Chloro-5-nitropyridineHCID 178422285HCID 178422285, compound

Product 1

HCID 178470411HCID 178470411, compound

Procedure

522 mg of 2-chloro-5-nitropyridine are added to a solution of 1 g of 3-(5,6-dimethyl-1H-benzimidazol-2-yl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-c]pyridine trifluoroacetate in 10 ml of pyridine. After stirring for 20 hours at ambient temperature, the reaction medium is concentrated under reduced pressure. The precipitate formed is recovered by filtration through sintered glass, washed with 3 times 15 ml of water, and dried under reduced pressure. The reaction crude obtained is purified by flash chromatography (SiO2, cyclohexane/EtOAc gradient 75/25 to 25/75). 450 mg of ethyl 6-(5-nitro-pyridin-2-yl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-c]pyridine-3-carboxylate are thus obtained in the form of a yellow powder, the characteristics of which are as follows:

Workup

  1. concentrationthe reaction medium is concentrated under reduced pressure
  2. customThe precipitate formed
  3. filtrationis recovered by filtration through sintered glass
  4. washwashed with 3 times 15 ml of water
  5. customdried under reduced pressure
  6. customThe reaction crude
  7. customobtained
  8. customis purified by flash chromatography (SiO2, cyclohexane/EtOAc gradient 75/25 to 25/75)

Sources & evidence

ORD record
ord-a1c0c1ad764546dfaafd576434f414c3
Source dataset
uspto-grants-2008_10
Patent number
US07435820B2

Reaction notes

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