Triethylamine → HCID 21993734, compound

HRID 1978513Notes

Reaction equation

HRID 1978513 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][C:40]([N:42]1[CH2:48][CH2:47][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][CH2:43]1)=[O:41].C1CCN2C(=NCCC2)CC1.C(N(CC)CC)C>C(#N)C>[C:52]1([CH2:51][CH2:50][CH2:49][N:45]2[CH2:46][CH2:47][CH2:48][N:42]([C:40]([CH2:39][NH:38][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:41])[CH2:43][CH2:44]2)[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=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 21994118HCID 21994118, compound

Product 1

HCID 21993734HCID 21993734, 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)propylcarbodimide hydrochloride. The mixture was stirred for one hour. To the reaction system was added a solution of 1.91 g (5.48 mmol.) of 1-(aminoacetyl)-4-(3-phenylpropan-1-yl)-2,3,5,6-tetrahydro-7H-1,4-diazepine dihydrochloride, 1.67 g (10.97 mmol.) of 1,8-diazabicyclo[5.4.0]unde-7-cene (DBU) and 0.7 ml (5.0 mmol.) of triethylamine in acetonitrile (20 ml). The mixture was stirred for further one hour. The solvent was distilled off under reduced pressure. To the residue was added water. The mixture was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution, followed by drying 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 an amorphous substance.

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 ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  7. dry with materialby drying over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a32b85bb386247038a219a51878cd860
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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