Hydrochloric Acid → HCID 22727088, compound

HRID 2086319Notes

Reaction equation

HRID 2086319 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][C:19](=[O:21])[N:18]([NH:22][CH:23]3[CH2:28][CH2:27][N:26]([C:29]4[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=4)[CH2:25][CH2:24]3)[CH:17]([CH2:36][C:37]([O:39]C)=[O:38])[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[OH-].[Na+].Cl>CO.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][C:19](=[O:21])[N:18]([NH:22][CH:23]3[CH2:24][CH2:25][N:26]([C:29]4[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=4)[CH2:27][CH2:28]3)[CH:17]([CH2:36][C:37]([OH:39])=[O:38])[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69545679HCID 69545679, compound

Product 1

HCID 22727088HCID 22727088, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 4-[(6-chloro-2-naphthyl)sulfonyl]-1-[[1-(2-methyl-4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazineacetate (1.17 g) obtained in Example 138 and a 2N aqueous solution of sodium hydroxide (2.0 ml) in methanol (20 ml) and 1,4-dioxane (10 m) was stirred at 40° C. for 2 hours. The reaction mixture was cooled, neutralized with 1N hydrochloric acid, and concentrated under reduced pressure. The residue was combined with saturated brine, extracted with a 10% methanol-containing dichloromethane, dried and concentrated. The residue obtained was crystallized from a mixture of ethanol and ethyl acetate to obtain the title compound (1.01 g) as colorless crystals.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with a 10% methanol-
  4. additioncontaining dichloromethane
  5. customdried
  6. concentrationconcentrated
  7. customThe residue obtained
  8. customwas crystallized from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-e3dfc4adbfd6460cbaf925624a9aea61
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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