HCID 22727199, compound → HCID 22727128, compound

HRID 2086289Notes

Reaction equation

HRID 2086289 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([S:14]([N:17]1[CH2:22][C:21](=[O:23])[N:20]([NH:24][CH:25]3[CH2:30][CH2:29][N:28]([C:31]4[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=4)[CH2:27][CH2:26]3)[CH:19]([C:37]([O:39][CH3:40])=[O:38])[CH2:18]1)(=[O:16])=[O:15])[CH:8]=[CH:7]2>C(Cl)Cl>[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([S:14]([N:17]1[CH2:22][C:21](=[O:23])[N:20]([NH:24][CH:25]3[CH2:26][CH2:27][N:28]([C:31]4[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=4)[CH2:29][CH2:30]3)[CH:19]([C:37]([O:39][CH3:40])=[O:38])[CH2:18]1)(=[O:15])=[O:16])[CH:8]=[CH:7]2

Participants

3

Reactant 1

HCID 22727199HCID 22727199, compound

Product 1

HCID 22727128HCID 22727128, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 4-[(6-chloro-2-naphthyl)sulfonyl]-6-oxo-1-[[1-(4-pyridinyl)-4-piperidinyl]amino]-2-piperazinecarboxylate dihydrochloride (0.26 g) was dissolved in methylene chloride (20 ml) and saturated aqueous sodium bicarbonate (20 ml) and the phases were separated. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure to obtain methyl 4-[(6-chloro-2-naphthyl)sulfonyl]-6-oxo-1-[[1-(4-pyridinyl)-4-piperidinyl]amino]-2-piperazinecarboxylate. This material was dissolved in a 37% aqueous solution of formaldehyde (3.1 ml) and formic acid (1.6 ml) and refluxed for 2 hours. The reaction mixture was cooled, made alkaline by adding a saturated aqueous sodium bicarbonate, extracted with dichloromethane, dried and concentrated. The residue thus obtained was purified by a column chromatography on a basic silica gel (ethyl acetate: methanol=10:1) to obtain methyl 4-[(6-chloro-2-naphthyl)sulfonyl]-1-[methyl[1-(4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazinecarboxylate as a pale yellow oil.

Workup

  1. customsaturated aqueous sodium bicarbonate (20 ml) and the phases were separated
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1e7be54cd31447c0b1b298b6ee360c5b
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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