Cyclohexylamine → HCID 22319655, compound

HRID 497677Notes

Reaction equation

HRID 497677 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].[CH:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][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][NH:22][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[N:7][NH:8]2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 10243527HCID 10243527, compound

Product 1

HCID 22319655HCID 22319655, compound

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 0.7 cm3 of cyclohexylamine. The reaction medium is refluxed for 2 hours and then concentrated to dryness under reduced pressure (2 kPa; 50° C.); the crude product obtained 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 (97/2.5/0.25 by volume). The fractions containing the expected product are combined and the residue is taken up in 20 cm3 of diisopropyl ether, filtered off and dried under reduced pressure (90 Pa; 45° C.) to give 492 mg of N-(6-chloro-1H-indazol-3-yl)-2-(cyclohexylamino)acetamide in the form of a white powder melting at 170° C.

Workup

  1. temperatureThe reaction medium is refluxed for 2 hours
  2. concentrationconcentrated to dryness under reduced pressure (2 kPa; 50° C.)
  3. customthe crude product obtained
  4. customis purified by chromatography under an argon pressure of 50 kPa
  5. washon a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with a methylene chloride/methanol/aqueous ammonia mixture (97/2.5/0.25 by volume)
  6. additionThe fractions containing the expected product
  7. filtrationfiltered off
  8. customdried under reduced pressure (90 Pa; 45° C.)

Sources & evidence

ORD record
ord-d8c0eab7b09240368768a7287a93724d
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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