Sodium Carbonate → HCID 69545896, compound

HRID 2086296Notes

Reaction equation

HRID 2086296 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]([NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([NH:21][CH:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[C:17]1=[O:34])(=[O:14])=[O:13])[CH:6]=[CH:5]2.[C:35](=O)([O-])[O-].[Na+].[Na+]>C=O.C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([N:21]([CH3:35])[CH:22]3[CH2:23][CH2:24][N:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[CH2:26][CH2:27]3)[C:17]1=[O:34])(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 69545567HCID 69545567, compound

Product 1

HCID 69545896HCID 69545896, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 712FormaldehydeSolvent

Procedure

(3S)-3-(6-Chloronaphthalene-2-sulfonylamino)-1-[1-(4-pyridyl)-4-piperidinylamino}-2-pyrrolidone (400 mg) was dissolved in a 37% aqueous solution of formaldehyde (11 ml) and formic acid (5 ml) and refluxed for 3 hours. The reaction mixture was cooled and made alkaline by adding an aqueous solution of sodium carbonate, extracted with dichloromethane, dried and concentrated. The residue was purified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1) and crystallized from dichloromethane to obtain the title compound (180 mg) as colorless crystals.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with dichloromethane
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1)
  7. customcrystallized from dichloromethane

Sources & evidence

ORD record
ord-f7b15c47b43e4913bbe7a14b7a0a4cbd
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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