Hydrochloric Acid → HCID 21993666, compound

HRID 1978413Notes

Reaction equation

HRID 1978413 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][NH:15][C:16]([C:18]1[S:28][C:27]2[N:29]3[C:20](=[CH:21][N:22]=[C:23]3[CH:24]=[CH:25][CH:26]=2)[CH:19]=1)=[O:17])=O)(C)(C)C.[ClH:30]>C(O)C>[ClH:30].[ClH:30].[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][NH:15][C:16]([C:18]1[S:28][C:27]2[N:29]3[C:20](=[CH:21][N:22]=[C:23]3[CH:24]=[CH:25][CH:26]=2)[CH:19]=1)=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21993821HCID 21993821, compound

Product 1

HCID 21993666HCID 21993666, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

While 3.605 g (16.519 mM) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid and 2.09 g (18.2 mM) of N-hydroxysuccinimide were stirred together in 100 ml of acetonitrile, 3.48 g (18.2 mM) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added and the mixture was stirred at room temperature for 2 hours. To this reaction mixture was added 3.45 ml (24.8 mM) of triethylamine as well as 2.83 g (24.8 mM) of 2-aminomethylpiperidine and the mixture was stirred at room temperature for one hour. Then, 5.41 g (24.8 mM) of di-tert-butyl dicarbonate was added and the mixture was stirred at room temperature for another hour. 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-2-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide. To this crude N-[1-(tert-butoxycarbonyl)piperidin-2-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide was added 5 ml of concentrated hydrochloric acid and the mixture was stirred at room temperature for 0.5 hour. After addition of ethanol, the mixture was stirred and the resulting precipitate was recovered and rinsed serially with ethanol and diethyl ether to provide the title compound.

Workup

  1. stirringthe mixture was stirred
  2. customthe resulting precipitate was recovered
  3. washrinsed serially with ethanol and diethyl ether

Sources & evidence

ORD record
ord-a88dc7cd14c64bf3b18b1d9c72c0d813
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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