Methanol → HCID 117778697, compound

HRID 2206562Notes

Reaction equation

HRID 2206562 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[NH:6][C:5](=[O:10])[C:4]=1[CH2:11][NH:12][C:13]([C:15]1[C:23]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[N:17]([CH:24]([C:26]2[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=2)[C:29]([OH:31])=[O:30])[CH3:25])[C:16]=1[CH3:35])=[O:14].[CH3:36]O>S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[NH:6][C:5](=[O:10])[C:4]=1[CH2:11][NH:12][C:13]([C:15]1[C:23]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[N:17]([CH:24]([C:26]2[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=2)[C:29]([O:31][CH3:36])=[O:30])[CH3:25])[C:16]=1[CH3:35])=[O:14]

Participants

4

Reactant 2

HCID 887MethanolHCID 117778720HCID 117778720, compound

Product 1

HCID 117778697HCID 117778697, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
70 °C

Procedure

To a solution of 3-(1-(3-(((4-methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-1-yl)ethyl)benzoic acid (20 mg, 0.042 mmol) in MeOH (6 mL) was added 2-3 drops of sulfuric acid. The mixture was stirred at 70° C. for 1 hour. The solvent was evaporated. The residue was dissolved in water (3 mL), quenched by saturated NaHCO3 solution, extracted with EA (10×3). The combined organic phase was dried by sodium sulfate, and then filtered. The filtrate was concentrated to give the title compound (20 mg, yield: 97%).

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in water (3 mL)
  3. customquenched by saturated NaHCO3 solution
  4. extractionextracted with EA (10×3)
  5. dry with materialThe combined organic phase was dried by sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ecdf453f97324f2581298fdc47c31627
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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