Acetonitrile → HCID 22319651, compound

HRID 497679Notes

Reaction equation

HRID 497679 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].[C:16](#[N:18])[CH3:17]>>[Cl:15][C:11]1[CH:10]=[C:9]2[C:14]([C:6]([NH:5][C:3](=[O:4])[CH2:2][N:18]3[CH:11]=[CH:10][CH:9]=[CH:14][CH:17]=[CH:16]3)=[N:7][NH:8]2)=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 10243527HCID 10243527, compound

Product 1

HCID 22319651HCID 22319651, compound

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 cm 3 of acetonitrile and 0.69 cm3 of hexamethyleneimine. The reaction medium is refluxed for 2 hours 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 ethyl acetate. The fractions containing the expected product are combined and the residue is taken up in 10 cm3 of diisopropyl ether, filtered off and dried under reduced pressure (90 Pa; 45° C.) to give 670 mg of N-(6-chloro-1H-indazol-3-yl)-1H-azepine-1-acetamide in the form of a yellow foam.

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 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 ethyl acetate
  5. additionThe fractions containing the expected product
  6. filtrationfiltered off
  7. customdried under reduced pressure (90 Pa; 45° C.)

Sources & evidence

ORD record
ord-1c86925bdd024d5f9cdbafd8d982c7f1
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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