Acetic Acid → HCID 69545567, compound

HRID 2086295Notes

Reaction equation

HRID 2086295 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]([N:21]=[C: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(O)(=O)C.C([BH3-])#N.[Na+]>CO>[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[CH2:23][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 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 69545703HCID 69545703, compound

Product 1

HCID 69545567HCID 69545567, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3S)-3-(6-Chloronaphthalene-2-sulfonylamino)-1-[1-(4-pyridyl)-4-piperidinylideneamino}-2-pyrrolidone (600 mg) was dissolved in methanol (40 ml), combined with acetic acid (761 mg) while cooling on ice, followed by sodium cyanoborohydride (300 mg) and stirred at room temperature for 30 minutes. The reaction mixture was concentrated and the residue was combined with an aqueous solution of sodium carbonate, extracted with dichloromethane, dried, concentrated and purified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1) and crystallized from ethyl acetate to obtain the title compound (576 mg) as colorless crystals.

Workup

  1. temperaturewhile cooling on ice
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with dichloromethane
  4. customdried
  5. concentrationconcentrated
  6. custompurified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1)
  7. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a8754ac3487b452cb3b756a72cb2213e
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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