Piperidine → HCID 69797481, compound

HRID 497720Notes

Reaction equation

HRID 497720 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:14]2[C:9](=[C:10]([F:16])[C:11]([F:15])=[CH:12][CH:13]=2)[NH:8][N:7]=1)=[O:4].[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C(#N)C>[F:15][C:11]1[C:10]([F:16])=[C:9]2[C:14]([C:6]([NH:5][C:3](=[O:4])[CH2:2][N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[N:7][NH:8]2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 22319653HCID 22319653, compound

Product 1

HCID 69797481HCID 69797481, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The process is performed as in Example 75, starting with 8.5 g of 2-chloro-N-(6,7-difluoro-1H-indazol-3-yl)acetamide, 200 cm3 of acetonitrile and 8.8 cm3 of piperidine. The reaction medium is refluxed for 1 hour, the precipitate formed is then filtered off on a sinter funnel and the crystals are taken up in 200 cm3 of ethyl acetate and 100 cm3 of water. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2 kPa; 50° C.). The crude product is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 3.5 cm), eluting with ethyl acetate. The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.); the residue is recristallized from a mixture of 50 cm3 of cyclohexane and 16 cm3 of ethyl acetate, filtered off and dried (90 Pa; 45° C.) to give 3.2 g of N-(6,7-difluoro-1H-indazol-3-yl)-1-piperidineacetamide in the form of white crystals melting at 158° C.

Workup

  1. temperatureThe reaction medium is refluxed for 1 hour
  2. customthe precipitate formed
  3. filtrationis then filtered off on a sinter funnel
  4. customThe organic phase is separated out
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2 kPa; 50° C.)
  8. customThe crude product is purified by chromatography under an argon pressure of 50 kPa
  9. washon a column of silica gel (particle size 40-60 μm; diameter 3.5 cm), eluting with ethyl acetate
  10. additionThe fractions containing the expected product
  11. customevaporated under reduced pressure (2 kPa; 50° C.)
  12. additionthe residue is recristallized from a mixture of 50 cm3 of cyclohexane and 16 cm3 of ethyl acetate
  13. filtrationfiltered off
  14. customdried (90 Pa; 45° C.)

Sources & evidence

ORD record
ord-cbcd86f2574b46dbb52a54ed0180fdcb
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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