Piperazine → HCID 9971655, compound

HRID 497680Notes

Reaction equation

HRID 497680 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:14]2[C:9](=[CH:10][C:11]([Cl:15])=[CH:12][CH:13]=2)[NH:8][N:7]=1)=[O:4].[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>C(#N)C>[Cl:15][C:11]1[CH:10]=[C:9]2[C:14]([C:6]([NH:5][C:3](=[O:4])[CH2:2][N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[N:7][NH:8]2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 10243527HCID 10243527, compound

Product 1

HCID 9971655HCID 9971655, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The process is performed as in Example 75, starting with 500 mg of 2-chloro-N-(6-chloro-1H-indazol-3-yl)acetamide, 15 cm3 of acetonitrile and 528 mg of piperazine. The reaction medium is refluxed for 1 hour and then 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 2.5 cm), eluting with a methylene chloride/methanol/aqueous ammonia mixture (90/10/1 by volume). The fractions containing the expected product are combined, concentrated under reduced pressure and then dried (90 Pa; 45° C.) to give 380 mg of N-(6-chloro-1H-indazol-3-yl)-1-piperazineacetamide in the form of a white foam.

Workup

  1. temperatureThe reaction medium is refluxed for 1 hour
  2. concentrationconcentrated to dryness under reduced pressure (2 kPa; 50° C.)
  3. customthe crude product is purified by chromatography under an argon pressure of 50 kPa
  4. washon a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with a methylene chloride/methanol/aqueous ammonia mixture (90/10/1 by volume)
  5. additionThe fractions containing the expected product
  6. concentrationconcentrated under reduced pressure
  7. customdried (90 Pa; 45° C.)

Sources & evidence

ORD record
ord-12c80e95dee84e2d9812cfa246ee9f82
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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