N-Hydroxysuccinimide → HCID 21993660, compound

HRID 1978425Notes

Reaction equation

HRID 1978425 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][CH2:42][N:43]1[CH2:48][CH2:47][CH:46]([CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:45][CH2:44]1>C(#N)C.C(N(CC)CC)C>[CH2:49]([CH:46]1[CH2:45][CH2:44][N:43]([CH2:42][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])[CH2:48][CH2:47]1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

7

Reactant 4

HCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10943925HCID 10943925, compoundHCID 21993909HCID 21993909, compound

Product 1

HCID 21993660HCID 21993660, 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 suspension of 2.19 g (6.86 mM) of 1-(4-aminobutan-1-yl)-4-benzylpiperidine dihydrochloride and 3.87 ml (27.8 mM) of triethylamine m 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, dried over MgSO4, and purified by column chromatography (methanol/ethyl acetate 30-50%) to provide the title compound as red-purple amorphous substance.

Workup

  1. additionTo this reaction mixture was added
  2. stirringthe mixture was further stirred for one hour
  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 30-50%)

Sources & evidence

ORD record
ord-4a8de262cfbe408aa868787e57455745
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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