N-Hydroxysuccinimide → HCID 21993828, compound

HRID 1978411Notes

Reaction equation

HRID 1978411 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][C:46](=[CH:49][CH2:50][NH2:51])[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][C:46](=[CH:49][CH2:50][NH:51][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 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10943925HCID 10943925, compoundHCID 21994082HCID 21994082, compound

Product 1

HCID 21993828HCID 21993828, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent

Procedure

While 1.56 g (7.17 mM) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid and 0.83 g (7.17 mM) of N-hydroxysuccinimide were stirred together in 50 ml of acetonitrile, 1.51 g (7.89 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 1.50 ml (10.8 mM) of triethylamine as well as a solution of the above crude 2-[1-(tert-butoxycarbonyl)piperidin-4-ylidene]ethylamine in 20 ml of acetonitrile and the mixture was stirred at room temperature for 2 hours. 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-[2-(1-(tert-butoxycarbonyl)piperidin-4-ylidene]ethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide. To this crude N-[2-(1-(tert-butoxycarbonyl)piperidin-4-ylidene)ethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide was added 4 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 at room temperature for 2 hours
  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-77940ebbe9e24caba81c19918765f659
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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