Water → HCID 137010690, compound

HRID 2206076Notes

Reaction equation

HRID 2206076 reaction equation
[C:1]([C:3]1[S:7][CH:6]=[C:5]([C:8]2[C:12]3[C:13](=[O:21])[NH:14][CH:15]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[C:11]=3[N:10]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:9]=2)[CH:4]=1)#[N:2].[C:27](=[O:30])([O-])[OH:28].[Na+].Cl.[NH2:33]O.O>CS(C)=O>[CH:22]1([N:10]2[C:11]3[C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][NH:14][C:13](=[O:21])[C:12]=3[C:8]([C:5]3[CH:4]=[C:3]([C:1]4[NH:33][C:27](=[O:30])[O:28][N:2]=4)[S:7][CH:6]=3)=[CH:9]2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 117988339HCID 117988339, compound

Product 1

HCID 137010690HCID 137010690, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 3-(5-cyano-3-thienyl)-1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (111 mg) obtained in Example 73 in DMSO (2 mL) were added sodium hydrogencarbonate (127 mg) and hydroxylamine hydrochloride (84 mg) at room temperature, and the mixture was stirred at 90° C. for 30 min. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To a solution of the residue in THF (2 mL) were added 1,1′-carbonyldiimidazole (73.5 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.068 mL) at room temperature, and the mixture was stirred overnight. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (90 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionTo a solution of the residue in THF (2 mL) were added 1,1′-carbonyldiimidazole (73.5 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.068 mL) at room temperature
  6. stirringthe mixture was stirred overnight
  7. additionTo the reaction mixture was added water
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-524f3ff3e0bb4c4b822b9aa0d49edd6d
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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