1H-1,2,4-Triazole → HCID 22319603, compound

HRID 497676Notes

Reaction equation

HRID 497676 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[CH:20]=[N:19][CH:18]=[N:17]1.C(=O)([O-])[O-].[K+].[K+]>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[CH:20]=[N:19][CH:18]=[N:17]3)=[N:7][NH:8]2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 10243527HCID 10243527, compound

Product 1

HCID 22319603HCID 22319603, compoundYield 21.2%

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, 423 mg of 1,2,4-triazole and 283 mg of potassium carbonate. The reaction medium is refluxed for 4 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 ethyl acetate. The fractions containing the expected product are combined, evaporated under reduced pressure (2 kPa; 50° C.) and dried (90 Pa; 45° C.) to give 120 mg of N-(6-chloro-1H-indazol-3-yl)-1H-1,2,4-triazole-1-acetamide in the form of a white powder melting above 260° C.

Workup

  1. temperatureThe reaction medium is refluxed for 4 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 ethyl acetate
  6. additionThe fractions containing the expected product
  7. customevaporated under reduced pressure (2 kPa; 50° C.)
  8. customdried (90 Pa; 45° C.)

Sources & evidence

ORD record
ord-0b567e3bcb374dd5abdf29e04a74a84a
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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