Hydrochloric Acid → HCID 21994182, compound

HRID 1978406Notes

Reaction equation

HRID 1978406 reaction equation
C(OC(N1CCC(C[NH:15][C:16]([C:18]2[S:28][C:27]3[N:29]4[C:20](=[CH:21][N:22]=[C:23]4[CH:24]=[CH:25][CH:26]=3)[CH:19]=2)=[O:17])CC1)=O)(C)(C)C.[ClH:30].[CH2:31](O)[CH3:32]>>[ClH:30].[ClH:30].[NH:22]1[CH2:23][CH2:24][CH:31]([CH2:32][C:21]2[N:22]=[C:23]3[N:29]4[C:27]([S:28][C:18]([C:16]([NH2:15])=[O:17])=[CH:19][C:20]=24)=[CH:26][CH:25]=[CH:24]3)[CH2:20][CH2:21]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 21994167HCID 21994167, compound

Product 1

HCID 21994182HCID 21994182, compound

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. stirringby stirring
  2. filtrationthe resulting precipitate was recovered by filtration
  3. washrinsed serially with ethanol and diethyl ether

Sources & evidence

ORD record
ord-a5fed355fa0b41caa59081c31249edd9
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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