Triethylamine → HCID 21993898, compound

HRID 1978519Notes

Reaction equation

HRID 1978519 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]([OH:15])=O)=[CH:4]2.ON1C(=O)CCC1=O.Cl.C(N=C=NCCCN(C)C)C.Cl.Cl.[NH2:38][CH2:39][CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][N:45]([C:48](=[O:55])[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:44][CH2:43]1.C1CCN2C(=NCCC2)CC1.C(N(CC)CC)C>C(#N)C>[C:48]([N:45]1[CH2:44][CH2:43][N:42]([CH2:41][CH2:40][CH2:39][NH:38][C:13]([C:5]2[S:6][C:7]3[N:12]4[C:3](=[CH:2][N:1]=[C:11]4[CH:10]=[CH:9][CH:8]=3)[CH:4]=2)=[O:15])[CH2:47][CH2:46]1)(=[O:55])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 80170N-HydroxysuccinimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10943925HCID 10943925, compoundHCID 21993726HCID 21993726, compound

Product 1

HCID 21993898HCID 21993898, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of 0.8 g (3.67 mmol.) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid and 0.84 g (8.8 mmol.) of N-hydroxysuccinimide in acetonitrile (15 ml) was added, at room temperature, 1.41 g (7.36 mmol.) of N-ethyl-N′-3-(N,N-dimethylamino)propylcarbodiimide hydrochloride. The mixture was stirred for 2 hours. To the reaction system was added a solution of 1.41 g (4.4 mmol.) of 4-(3-aminopropan-1-yl)-1-benzoylpiperazin dihydrochloride, 1.34 g (8.8 mmol.) of 1,8-diazabicyclo[5.4.0]unde-7-cene (DBU) and 1.0 ml (7.17 mmol.) of triethylamine in acetonitrile (15 ml). The mixture was stirred for further 2 hours. The solvent was distilled off under reduced pressure. To the residue was added water, which was subjected to extraction with ethyl acetate (a small volume of ethanol was also used). The organic layer was washed with a saturated aqueous saline solution, dried over magnesium sulfate and subjected to to distillation under reduced pressure. The residue was subjected to fractional purification by means of a column chromatography (methanol/ethyl acetate 30-40%), followed by distilling off the solvent under reduced pressure to afford the object compound as a reddish purple crystalline product. The yield was 0.738 g (45%).

Workup

  1. additionwas added, at room temperature
  2. stirringThe mixture was stirred for further 2 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionTo the residue was added water, which
  5. extractionwas subjected to extraction with ethyl acetate (a small volume of ethanol
  6. washThe organic layer was washed with a saturated aqueous saline solution
  7. dry with materialdried over magnesium sulfate
  8. distillationsubjected to to distillation under reduced pressure
  9. customThe residue was subjected to fractional purification by means of a column chromatography (methanol/ethyl acetate 30-40%)
  10. distillationby distilling off the solvent under reduced pressure
  11. customto afford the object compound as a reddish purple crystalline product

Sources & evidence

ORD record
ord-ae9ec412db0a452cad3db50667b9faee
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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