Hydrochloric Acid → HCID 53784070, compound

HRID 2395811Notes

Reaction equation

HRID 2395811 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([S:15]([NH:18][CH:19]1[CH2:23][CH2:22][N:21]([CH:24]([C:34]([N:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)=[O:35])[CH2:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=3)[C:20]1=[O:42])(=[O:17])=[O:16])[CH:7]=[CH:6]2.[SH2:43].Cl>C(N(CC)CC)C.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([S:15]([NH:18][CH:19]1[CH2:23][CH2:22][N:21]([CH:24]([C:34]([N:36]3[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]3)=[O:35])[CH2:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([NH2:33])=[S:43])=[CH:28][CH:27]=3)[C:20]1=[O:42])(=[O:17])=[O:16])[CH:7]=[CH:6]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 402Hydrogen SulfideHCID 18989286HCID 18989286, compound

Product 1

HCID 53784070HCID 53784070, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

4.6 g (7.78 mmol) of 3-(6,7-dimethoxynaphthalene-2-sulfonylamino)-1-[2-(4-cyanophenyl)-1-piperidinocarbonylethyl]-2-pyrrolidinone were dissolved in 5 ml of triethylamine and 80 ml of pyridine, and hydrogen sulfide was passed into saturation. The mixture was left to stand overnight and subsequently added dropwise to a mixture of 600 g of ice and 100 ml of concentrated hydrochloric acid. The precipitate was filtered off with suction and dissolved in THF, and the solution was dried over magnesium sulfate and concentrated. The residue was mixed with ether and, after stirring at room temperature for 30 min, the precipitate was filtered off with suction. The slightly impure 3-(6,7-dimethoxynaphthalene-2-sulfonylamino)-1-[2-(4-aminothiocarbonylphenyl)-1-piperidinocarbonylethyl]-2-pyrrolidinone was used without further purification in the next stage.

Workup

  1. waitThe mixture was left
  2. filtrationThe precipitate was filtered off with suction
  3. dissolutiondissolved in THF
  4. dry with materialthe solution was dried over magnesium sulfate
  5. concentrationconcentrated
  6. additionThe residue was mixed with ether
  7. filtrationthe precipitate was filtered off with suction
  8. customThe slightly impure 3-(6,7-dimethoxynaphthalene-2-sulfonylamino)-1-[2-(4-aminothiocarbonylphenyl)-1-piperidinocarbonylethyl]-2-pyrrolidinone was used without further purification in the next stage

Sources & evidence

ORD record
ord-197403a17feb428ca82fb715606563ac
Source dataset
uspto-grants-1996_02
Patent number
US05489583

Reaction notes

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