N-Hydroxysuccinimide → HCID 21993743, compound

HRID 1978423Notes

Reaction equation

HRID 1978423 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.[NH2:36][CH2:37][CH2:38][CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][CH:44]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:43][CH2:42]1>C(#N)C.C(N(CC)CC)C>[C:47]1([CH:44]2[CH2:43][CH2:42][N:41]([CH2:40][CH2:39][CH2:38][CH2:37][NH:36][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])[CH2:46][CH2:45]2)[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

7

Reactant 4

HCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10943925HCID 10943925, compoundHCID 23004174HCID 23004174, compound

Product 1

HCID 21993743HCID 21993743, 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 reaction mixture was added a solution of 1.60 g (6.89 mM) of 1-(4-aminobutan-1-yl)-4-phenylpiperidine and 1.3 ml (9.33 mM) of triethylamine in acetonitrile (5 ml) and the mixture was further stirred for one hour. 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 and dried over MgSO4. This crude product was purified by column chromatography (methanol/ethyl acetate 20-50-80%) to provide the title compound as red-purple solid.

Workup

  1. stirringthe mixture was further stirred for one hour
  2. distillationThe solvent was then 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. customThis crude product was purified by column chromatography (methanol/ethyl acetate 20-50-80%)

Sources & evidence

ORD record
ord-389fb220730444e1b99c1144a9045d5e
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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