Benzylamine → HCID 22319614, compound

HRID 497678Notes

Reaction equation

HRID 497678 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].[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[C:17]1([CH2:16][NH:23][CH2:2][C:3]([NH:5][C:6]2[C:14]3[C:9](=[CH:10][C:11]([Cl:15])=[CH:12][CH:13]=3)[NH:8][N:7]=2)=[O:4])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 10243527HCID 10243527, compound

Product 1

HCID 22319614HCID 22319614, 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 0.67 cm3 of benzylamine. The reaction medium is refluxed for 1 hour and the precipitate formed is filtered off, washed with 5 cm3 of acetonitrile and 5 cm3 of methylene chloride, then 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 305 mg of 2-[(phenylmethyl)amino]-N-(6-chloro-1H-indazol-3-yl)acetamide in the form of a white powder melting at 156° C.

Workup

  1. temperatureThe reaction medium is refluxed for 1 hour
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. washwashed with 5 cm3 of acetonitrile and 5 cm3 of methylene chloride
  5. custompurified by chromatography under an argon pressure of 50 kPa
  6. 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)
  7. additionThe fractions containing the expected product
  8. filtrationfiltered off
  9. customdried under reduced pressure (90 Pa; 45° C.)

Sources & evidence

ORD record
ord-7cd67b2143eb4b6ca55d9dd5432ab616
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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