N,N-Dimethylethylenediamine → HCID 22319579, compound

HRID 497684Notes

Reaction equation

HRID 497684 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].[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][NH2:20]>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:20][CH2:19][CH2:18][N:17]([CH3:21])[CH3:16])=[N:7][NH:8]2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 10243527HCID 10243527, compound

Product 1

HCID 22319579HCID 22319579, 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 0.68 cm3 of N,N-dimethylethylenediamine. 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 a methylene chloride/methanol/aqueous ammonia mixture (95/5/1 by volume). The fractions containing the expected product are combined, concentrated under reduced pressure and then dried (90 Pa; 45° C.) to give 113 mg of N-(6-chloro-1H-indazol-3-yl)-2-[[2-(dimethylamino)ethyl]amino]acetamide in the form of a white solid melting at 104° 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 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 (95/5/1 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-cf10365a52824ac3a57639da3808b6f7
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

Loading…