Triethylamine → HCID 21994032, compound

HRID 1978521Notes

Reaction equation

HRID 1978521 reaction equation
[N:1]1[CH:2]=[C:3]2[N:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=13)[S:6][C:5]([C:13]([O:15]CC)=O)=[CH:4]2.ON1C(=O)CCC1=O.C(N=C=NCCCN(C)C)C.Cl.Cl.[NH2:39][CH2:40][CH2:41][N:42]1[C:47](=[O:48])[CH2:46][N:45]([CH2:49][CH2:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH2:44][C:43]1=[O:58].C(N(CC)CC)C>C(#N)C.C(Cl)(Cl)Cl>[O:58]=[C:43]1[CH2:44][N:45]([CH2:49][CH2:50][CH2:51][C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[CH2:46][C:47](=[O:48])[N:42]1[CH2:41][CH2:40][NH:39][C:13]([C:5]1[S:6][C:7]2[N:12]3[C:3](=[CH:2][N:1]=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH:4]=1)=[O:15]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 12038723HCID 12038723, compoundHCID 21993878HCID 21993878, compound

Product 1

HCID 21994032HCID 21994032, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 0.8 g (3.67 mmol.) of ethyl 5-thia-1,8b-diazaacenaphthylene-4-carboxylate and 0.84 g (7.30 mmol.) of N-hydroxysuccinimide in acetonitrile (10 ml) was added, at room temperature, 1.41 g (7.36 mmol.) of N-ethyl-N′-3-(N,N-dimethylamino)propylcarbodiimide. The mixture was stirred for 2 hours. To the reaction system was added a solution of 1.66 g (4.77 mmol.) of 1-(2-aminoethan-1-yl)-2,6-dioxo-4-(3-phenylpropan-1-yl)piperazine.dihydrochloride and 2.7 ml (19.4 mmol.) of triethylamine in chloroform (5 ml). The mixture was stirred for further one hour. The solvent was distilled off under reduced pressure. To the residue was added water, and the mixture was subjected to extraction with chloroform. The organic layer was washed with a saturated aqueous saline solution, which was dried over magnesium sulfate. The concentrate was purified by means of a column chromatography (methanol/ethyl acetate 20%) to afford the object compound as a reddish amorphous product. The yield was 1.56 g (89%).

Workup

  1. additionwas added, at room temperature
  2. stirringThe mixture was stirred for further one hour
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionTo the residue was added water
  5. extractionthe mixture was subjected to extraction with chloroform
  6. washThe organic layer was washed with a saturated aqueous saline solution, which
  7. dry with materialwas dried over magnesium sulfate
  8. customThe concentrate was purified by means of a column chromatography (methanol/ethyl acetate 20%)
  9. customto afford the object compound as a reddish amorphous product

Sources & evidence

ORD record
ord-6b7e2d9de88b43838fe384c5dc4f6ffb
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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