Water → HCID 67306576, compound

HRID 2039652Notes

Reaction equation

HRID 2039652 reaction equation
Cl.[F:2][C:3]([F:20])([F:19])[C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:18]=[C:13]3[CH2:14][NH:15][CH2:16][CH2:17][C:12]3=[N:11]2)=[N:8][CH:9]=1.C(N(CC)CC)C.[Cl:28][CH2:29][C:30](Cl)=[O:31].O>ClCCl>[Cl:28][CH2:29][C:30]([N:15]1[CH2:16][CH2:17][C:12]2=[N:11][N:10]([C:7]3[CH:6]=[CH:5][C:4]([C:3]([F:19])([F:2])[F:20])=[CH:9][N:8]=3)[CH:18]=[C:13]2[CH2:14]1)=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 68313808HCID 68313808, compound

Product 1

HCID 67306576HCID 67306576, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g of 2-(5-trifluoromethylpyridin-2-yl)-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine hydrochloride is suspended in 12 ml of dichloromethane, in a round-bottomed flask equipped with a magnetic stirrer. 0.95 ml of triethylamine is added and the mixture is brought to 0° C. At 0° C., 0.33 ml of chloroacetyl chloride, i.e. the compound of general formula (V) in which Hal=Hal′=Cl and n=1, is run in dropwise. The mixture is left to react for 1 and a half hours and is poured into water. Extraction is carried out with dichloromethane. The organic phase is dried over Na2SO4, filtered and evaporated under vacuum. The residue is purified by flash chromatography on a Biotage® column, elution being carried out with 9 cyclohexane/1 ethyl acetate. 1.08 g of the title compound are obtained in the form of a yellow solid.

Workup

  1. customequipped with a magnetic stirrer
  2. customis brought to 0° C
  3. customAt 0° C.
  4. waitThe mixture is left
  5. customto react for 1 and a half hours
  6. extractionExtraction
  7. dry with materialThe organic phase is dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under vacuum
  10. customThe residue is purified by flash chromatography on a Biotage® column, elution

Sources & evidence

ORD record
ord-f88f13d5e51546b79c112a26fa00b44f
Source dataset
uspto-grants-2013_11
Patent number
US08580790B2

Reaction notes

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