N-Hydroxysuccinimide → HCID 21993953, compound

HRID 1978427Notes

Reaction equation

HRID 1978427 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][N:42]1[CH2:47][CH2:46][CH:45]([CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:44][CH2:43]1>C(#N)C.C(N(CC)CC)C>[CH2:48]([CH:45]1[CH2:44][CH2:43][N: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])[CH2:47][CH2:46]1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

7

Reactant 4

HCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10943925HCID 10943925, compoundHCID 21994054HCID 21994054, compound

Product 1

HCID 21993953HCID 21993953, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a suspension of 1.0 g (4.58 mM) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid and 1.05 g (9.12 mM) of N-hydroxysuccinimide in acetonitrile (10 ml) was added 1.76 g (9.18 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 mixture was added a suspension of 2.09 g (6.85 mM) of 1-(3-aminopropan-1-yl)-4-benzylpiperidine dihydrochloride and 3.87 ml (27.8 mM) of triethylamine in acetonitrile (5 ml) and the mixture was further stirred for 30 minutes. The solvent was then 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 20-40-60%) to provide the title compound as red-purple amorphous substance.

Workup

  1. additionTo this mixture was added
  2. stirringthe mixture was further stirred for 30 minutes
  3. distillationThe solvent was then distilled off under reduced pressure
  4. additionthe residue was diluted with water
  5. extractionextracted with chloroform
  6. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over MgSO4
  8. custompurified by column chromatography (methanol/ethyl acetate 20-40-60%)

Sources & evidence

ORD record
ord-0de5dc7eba954ef6a95dda3a95b22267
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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