Triethylamine → HCID 21993655, compound

HRID 1978517Notes

Reaction equation

HRID 1978517 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][CH2:42][N:43]1[CH2:48][CH2:47][N:46]([C:49](=[O:56])[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:45][CH2:44]1.N12CCCNC1CCCC=C2.C(N(CC)CC)C>C(#N)C>[C:49]([N:46]1[CH2:45][CH2:44][N:43]([CH2:42][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])[CH2:48][CH2:47]1)(=[O:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 98128211,8-Diazabicyclo[5.4.0]undec-2-eneHCID 10943925HCID 10943925, compoundHCID 21993959HCID 21993959, compound

Product 1

HCID 21993655HCID 21993655, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of 1.0 g (4.58 mmol.) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid and 1.05 g (9.12 mmol.) of N-hydroxysuccinimide in acetonitrile (15 ml) was added, at room temperature, 1.76 g (9.18 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 1.68 g (5.5 mmol.) of 4-(4-aminobutan-1-yl)-1-benzoylpiperazine dihydrochloride, 1.68 g (11.04 mmol.) of 1,8-diazabicyclo[5.4.0]undecene (DBU) and 1.5 ml (10.76 mmol.) of triethylamine in acetonitrile (10 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 and dried over magnesium sulfate, followed by distilling off the solvent. The residue was purified by means of a column chromatography (methanol/ethyl acetate 20-30%) to give the object compound as a reddish amorphous product. The yield was 1.25 g (59%).

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. distillationby distilling off the solvent
  9. customThe residue was purified by means of a column chromatography (methanol/ethyl acetate 20-30%)
  10. customto give the object compound as a reddish amorphous product

Sources & evidence

ORD record
ord-82c213d1ed504f87bb99c639bd8b239e
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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