N-Hydroxysuccinimide → HCID 21994167, compound

HRID 1978405Notes

Reaction equation

HRID 1978405 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.[C:36]([O:40][C:41]([N:43]1[CH2:48][CH2:47][CH:46]([CH2:49][NH2:50])[CH2:45][CH2:44]1)=[O:42])([CH3:39])([CH3:38])[CH3:37].C(=O)([O-])O.[Na+]>C(#N)C.C(N(CC)CC)C>[C:36]([O:40][C:41]([N:43]1[CH2:48][CH2:47][CH:46]([CH2:49][NH:50][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])[CH2:45][CH2:44]1)=[O:42])([CH3:39])([CH3:38])[CH3:37]

Participants

8

Reactant 5

HCID 80170N-HydroxysuccinimideHCID 516892Sodium BicarbonateHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10943925HCID 10943925, compound

Product 1

HCID 21994167HCID 21994167, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

While 26.48 g (121.3 mM) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid and 15.4 g (133 mM) of N-hydroxysuccinimide were stirred together in 250 ml of acetonitrile, 25.6 g (133 mM) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added and the mixture was stirred at room temperature for 6 hours. To this reaction mixture was added 20.3 ml (146 mM) of triethylamine as well as 27.3 g (127 mM) of 1-(tert-butoxycarbonyl)piperidin-4-ylmethylamine and the mixture was stirred at room temperature overnight. This reaction mixture was poured in aqueous solution of sodium hydrogen carbonate and extracted with 3 portions of ethyl acetate. The organic layers were pooled and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate to ethyl acetate-methanol=9:1) to provide crude N-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide. To this crude N-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide was added 30 ml of concentrated hydrochloric acid and the mixture was stirred at room temperature for one hour. To this reaction mixture was added ethanol, followed by stirring, and the resulting precipitate was recovered by filtration and rinsed serially with ethanol and diethyl ether to provide the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionextracted with 3 portions of ethyl acetate
  3. dry with materialdried over MgSO4
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f5d47209b6d34662bbe4aac4a8b15bde
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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