N-Hydroxysuccinimide → HCID 21994017, compound

HRID 1978429Notes

Reaction equation

HRID 1978429 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.Cl.[NH2:39][CH2:40][CH2:41][CH2:42][CH2:43][N:44]1[CH2:49][CH2:48][N:47]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:46][CH2:45]1>C(#N)C.C(O)C.C(N(CC)CC)C>[C:50]1([N:47]2[CH2:46][CH2:45][N:44]([CH2:43][CH2:42][CH2:41][CH2:40][NH:39][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])[CH2:49][CH2:48]2)[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1

Participants

8

Reactant 4

HCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10943925HCID 10943925, compoundHCID 21994133HCID 21994133, compound

Product 1

HCID 21994017HCID 21994017, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of 1.0 g (4.58 mM) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid and 0.90 g (7.82 mM) of N-hydroxysuccinimide in acetonitrile (10 ml) was added 1.51 g (7.88 mM) of N-ethyl-N′-3-(N,N-dimethylamino)propylcarbodiimide hydrochloride at room temperature and the mixture was stirred at the prevailing temperature for 2 hours. To this reaction mixture was added a solution of 2.02 g (5.89 mM) of 1-(4-aminobutan-1-yl)-4-phenylpiperazine trihydrochloride and 4.1 ml (29.4 mM) of triethylamine in ethanol (10 ml) and the mixture was further stirred for one hour. The solvent was distilled off under reduced pressure and the residue was diluted with water and extracted with chloroform. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over MgSO4, and purified by column chromatography (methanol/ethyl acetate 50% methanol-chloroform=1:10). After concentration, ethanol was added to the residue and the resulting crystal crop was harvested by filtration to provide the title compound as rouge-colored crystals.

Workup

  1. stirringthe mixture was further stirred for one hour
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over MgSO4
  7. custompurified by column chromatography (methanol/ethyl acetate 50% methanol-chloroform=1:10)
  8. concentrationAfter concentration, ethanol
  9. additionwas added to the residue
  10. filtrationthe resulting crystal crop was harvested by filtration

Sources & evidence

ORD record
ord-9bad0de5e5ec473b876f031fe51aec53
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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