N-Hydroxysuccinimide → HCID 21994004, compound

HRID 1978487Notes

Reaction equation

HRID 1978487 reaction equation
Cl.[N:2]1[CH:3]=[C:4]2[N:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=13)[S:7][C:6]([C:14]([OH:16])=O)=[CH:5]2.ON1C(=O)CCC1=O.Cl.C(N=C=NCCCN(C)C)C.Cl.Cl.[NH2:39][CH2:40][C:41]1[CH:60]=[CH:59][C:44]([CH2:45][N:46]2[CH2:51][CH2:50][CH:49]([CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[CH2:48][CH2:47]2)=[CH:43][CH:42]=1>C(#N)C.C(N(CC)CC)C>[CH2:52]([CH:49]1[CH2:50][CH2:51][N:46]([CH2:45][C:44]2[CH:43]=[CH:42][C:41]([CH2:40][NH:39][C:14]([C:6]3[S:7][C:8]4[N:13]5[C:4](=[CH:3][N:2]=[C:12]5[CH:11]=[CH:10][CH:9]=4)[CH:5]=3)=[O:16])=[CH:60][CH:59]=2)[CH2:47][CH2:48]1)[C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1

Participants

7

Reactant 4

HCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21994179HCID 21994179, compoundHCID 70243775HCID 70243775, compound

Product 1

HCID 21994004HCID 21994004, 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 hydrochloride 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 for 2 hours. To this reaction mixture was added a solution of 1.88 g (5.12 mM) of 1-[4-(aminomethyl)benzyl]-4-benzylpiperidine dihydrochloride and 0.55 ml (3.95 mM) of triethylamine in acetonitrile (20 ml) and the mixture was further stirred for 4 hours. The solvent was then distilled off under reduced pressure and the residue was diluted with water and extracted with ethyl acetate (a small amount of ethanol was additionally used). The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. The resulting crude product was purified by column chromatography (methanol/ethyl acetate 20%) to provide the title compound as red amorphous substance.

Workup

  1. stirringthe mixture was further stirred for 4 hours
  2. distillationThe solvent was then distilled off under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate (a small amount of ethanol
  5. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over MgSO4
  7. customThe resulting crude product was purified by column chromatography (methanol/ethyl acetate 20%)

Sources & evidence

ORD record
ord-8e6c86284e114c6cafb666fb09b8c406
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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