Hydrochloric Acid → 4-[(6-Chloro-2-naphthyl)sulfonyl]-1-[methyl[1-(2-methyl-4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazinecarboxylic Acid

HRID 2086315Notes

Reaction equation

HRID 2086315 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][C:20](=[O:22])[N:19]([N:23]([CH3:37])[CH:24]3[CH2:29][CH2:28][N:27]([C:30]4[CH:35]=[CH:34][N:33]=[C:32]([CH3:36])[CH:31]=4)[CH2:26][CH2:25]3)[CH:18]([C:38]([O:40]C)=[O:39])[CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.[OH-].[Na+].Cl>CO>[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][C:20](=[O:22])[N:19]([N:23]([CH3:37])[CH:24]3[CH2:25][CH2:26][N:27]([C:30]4[CH:35]=[CH:34][N:33]=[C:32]([CH3:36])[CH:31]=4)[CH2:28][CH2:29]3)[CH:18]([C:38]([OH:40])=[O:39])[CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22727060HCID 22727060, compound

Product 1

HCID 227271054-[(6-Chloro-2-naphthyl)sulfonyl]-1-[methyl[1-(2-methyl-4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazinecarboxylic AcidYield 84.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-[(6-chloro-2-naphthyl)sulfonyl]-1-[methyl[1-(2-methyl-4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazinecarboxylate hydrochloride (0.22 g) obtained in Example 128 and a 1N aqueous solution of sodium hydroxide (1.4 ml) in methanol (4.0 ml) was stirred at 40° C. for 30 minutes. The reaction mixture was cooled, and the reaction system was adjusted at pH 5 with 1N hydrochloric acid, and then concentrated under reduced pressure. The residue was purified on a CHP-20 column (water→1% conc. aqueous ammonia-containing 25% aqueous solution of acetonitrile) to obtain the title compound (0.17 g) as a colorless powder.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified on a CHP-20 column (water→1% conc. aqueous ammonia-containing 25% aqueous solution of acetonitrile)

Sources & evidence

ORD record
ord-7ae1d2305b7d473382d3a38497a02f55
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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