Thiomorpholine → HCID 67042704, compound

HRID 497682Notes

Reaction equation

HRID 497682 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[CH2:21][CH2:20][S: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][N:16]3[CH2:21][CH2:20][S:19][CH2:18][CH2:17]3)=[N:7][NH:8]2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 10243527HCID 10243527, compound

Product 1

HCID 67042704HCID 67042704, 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 0.62 cm3 of thiomorpholine. The reaction medium is refluxed for 2 hours, the precipitate formed is filtered off and the filtrate is 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 cyclohexane/ethyl acetate mixture (50/50 by volume). The fractions containing the expected product are combined, evaporated under reduced pressure (2 kPa; 50° C.) and dried (90 Pa; 45° C.) to give 560 mg of N-(6-chloro-1H-indazol-3-yl)thiomorpholine-4-acetamide in the form of a pale yellow foam.

Workup

  1. temperatureThe reaction medium is refluxed for 2 hours
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. concentrationthe filtrate is concentrated to dryness under reduced pressure (2 kPa; 50° C.)
  5. customthe crude product obtained
  6. customis purified by chromatography under an argon pressure of 50 kPa
  7. washon a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with a cyclohexane/ethyl acetate mixture (50/50 by volume)
  8. additionThe fractions containing the expected product
  9. customevaporated under reduced pressure (2 kPa; 50° C.)
  10. customdried (90 Pa; 45° C.)

Sources & evidence

ORD record
ord-75a212d66b9c4713b13ead7b0216cbc3
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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