Diisopropylethylamine → HCID 21190156, compound

HRID 1068723Notes

Reaction equation

HRID 1068723 reaction equation
[F:1][C:2]([F:17])([F:16])[S:3]([NH:6][CH2:7][CH2:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)(=[O:5])=[O:4].C(N(CC)C(C)C)(C)C.C([O:29][C:30]([C:32]1[N:37]2[C:38]([C:41](=[O:46])C(Cl)(Cl)Cl)=[CH:39][N:40]=[C:36]2[CH:35]=[CH:34][CH:33]=1)=O)C>C(#N)C>[F:17][C:2]([F:16])([F:1])[S:3]([NH:6][CH2:7][CH2:8][C:9]1[CH:15]=[CH:14][C:12]([N:13]2[C:30](=[O:29])[C:32]3[N:37]4[C:38](=[CH:39][N:40]=[C:36]4[CH:35]=[CH:34][CH:33]=3)[C:41]2=[O:46])=[CH:11][CH:10]=1)(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15472383HCID 15472383, compoundHCID 21190247HCID 21190247, compound

Product 1

HCID 21190156HCID 21190156, compoundYield 6.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1.18 g (4.4 mmol) of 4-[2-(trifluoromethanesulfonamido)ethan-1-yl]aniline and 0.68 g (5.3 mmol) of N,N-diisopropylethylamine in 20 ml of acetonitrile was added a solution of 1.53 g (4.4 mmol) of 5-ethoxycarbonyl-3-trichloroacetylimidazo[1,2-a]pyridine. The mixture was heated for 38 hours under reflux. After cooling, and the solvent was distilled off. To the residue was added chloroform. The mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to give 130 mg of the desired compound (6.8%, brown solid).

Workup

  1. temperatureThe mixture was heated for 38 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled off
  5. additionTo the residue was added chloroform
  6. washThe mixture was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customThe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-82ba1e7d415941d0826774cd87b3e9cd
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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