Triethylamine → HCID 70243698, compound

HRID 1978515Notes

Reaction equation

HRID 1978515 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=N[CH2:30][CH2:31][CH2:32]N(C)C)C.Cl.Cl.C1(CCC[N:47]2[CH2:52][CH2:51][CH:50]([NH:53][C:54](=[O:57])[CH2:55][NH2:56])[CH2:49][CH2:48]2)C=CC=CC=1.[CH2:58]1[CH2:68][CH2:67]N2[C:61](=NCCC2)[CH2:60][CH2:59]1.C(N(CC)CC)C>C(#N)C>[C:58]1([CH2:32][CH2:31][CH2:30][CH:55]([C:54]([NH:53][CH:50]2[CH2:49][CH2:48][NH:47][CH2:52][CH2:51]2)=[O:57])[NH:56][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])[CH:59]=[CH:60][CH:61]=[CH:67][CH:68]=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 21993867HCID 21993867, compound

Product 1

HCID 70243698HCID 70243698, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of 0.5 g (2.29 mmol.) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid and 0.53 g (4.61 mmol.) of N-hydroxysuccinimide in acetonitrile (10 ml) was added, at room temperature, 0.88 g (4.59 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 0.96 g (2.76 mmol.) of N-[1-(3-phenylpropan-1-yl)piperidin-4-yl]-aminoacetamide dihydrochloride, 0.84 g (5.52 mmol.) of 1,8-diazabicyclo[5.4.0]unde-7-cene (DBU) and 0.4 ml (2.87 mmol.) of triethylamine in acetonitrile (10 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 and dried over magnesium sulfate, followed by distilling off the solvent under reduced pressure to leave a crude product. The crude product was purified by means of a column chromatography (methanol/ethyl acetate 1:3→1:1→3:1), followed by recrystallization from ethyl acetate to afford the object compound as purple crystals. The yield was 303.2 mg (28%).

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
  7. dry with materialdried over magnesium sulfate
  8. distillationby distilling off the solvent under reduced pressure
  9. customto leave a crude product
  10. customThe crude product was purified by means of a column chromatography (methanol/ethyl acetate 1:3→1:1→3:1)
  11. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-2165677846ad482786342bbeee286836
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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