Triethylamine → HCID 21994063, compound

HRID 1978511Notes

Reaction equation

HRID 1978511 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.O[N:17]1[C:21](=O)[CH2:20][CH2:19][C:18]1=[O:23].Cl.C(N=C=N[CH2:30][CH2:31][CH2:32]N(C)C)C.[CH2:36]1[CH2:46][CH2:45][N:44]2[C:39](=NC[CH2:42][CH2:43]2)[CH2:38][CH2:37]1.C([N:49](CC)CC)C>C(#N)C>[C:36]1([CH2:37][CH2:38][CH2:39][N:44]2[CH2:43][CH2:42][N:17]([C:18]([CH2:19][NH:49][C:13]([C:5]3[S:6][C:7]4[N:12]5[C:3](=[CH:2][N:1]=[C:11]5[CH:10]=[CH:9][CH:8]=4)[CH:4]=3)=[O:15])=[O:23])[CH2:21][CH2:20]2)[CH:46]=[CH:45][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 5

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

Product 1

HCID 21994063HCID 21994063, 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 (20 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 1.5 hour. To the reaction system was added a solution of 1.68 g (5.03 mmol.) of 1-aminoacetyl-4-(3-phenylpropan-1-yl)piperazine dihydrochloride, 1.53 g (10.05 mmol.) of 1,8-diazabicyclo[5.4.0]unde-7-cene (DBU) and 0.7 ml (5.02 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. The mixture was subjected to extraction with ethyl acetate (a small volume of ethanol was also used). The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution, which was dried over magnesium sulfate. The solvent was distilled off under reduced pressure to leave a crude product, which was purified by means of a column chromatography (methanol/ethyl acetate 30-50%) to afford the object compound as a reddish amorphous substance. The yield was 1.32 g (62%).

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
  5. extractionThe mixture was subjected to extraction with ethyl acetate (a small volume of ethanol
  6. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  7. dry with materiala saturated aqueous saline solution, which was dried over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-622a90751a0b424c89faf392bc3d9f90
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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