Methanol → HCID 178524910, compound

HRID 1471812Notes

Reaction equation

HRID 1471812 reaction equation
[O:1]=[C:2]1[C:10]2[C:5]([C:6]3[C:7](=[C:11]([C:14]([O:16]CC)=[O:15])[NH:12][CH:13]=3)[NH:8][CH:9]=2)=[N:4][N:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CO.C1COCC1.[Li+].[OH-]>O>[O:1]=[C:2]1[C:10]2[C:5]([C:6]3[C:7](=[C:11]([C:14]([OH:16])=[O:15])[NH:12][CH:13]=3)[NH:8][CH:9]=2)=[N:4][N:3]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 178470379HCID 178470379, compound

Product 1

HCID 178524910HCID 178524910, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

Ethyl 3-oxo-2-phenyl-2,3,5,7-tetrahydropyrazolo[3,4-d]pyrrolo[3,4-b]pyridine-6-carboxylate was dissolved into a mixture of methanol, THF and H2O (1:1:1, 0.2 M). LiOH (5 eq.) was added and the reaction was heated at 45° C. for 17 hours. After cooling to room temperature the reaction was concentrated to dryness. 10% HCl (aq.) was added and the precipitate was collected, affording the title compound as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.87-7.21 (m, 1H) 7.25-7.52 (m, 2H) 7.60-7.85 (m, 1H) 8.13 (br. s., 3H) 11.56-11.92 (m, 1H) 12.90-13.17 (m, 1H)

Workup

  1. temperatureAfter cooling to room temperature the reaction
  2. concentrationwas concentrated to dryness
  3. addition10% HCl (aq.) was added
  4. customthe precipitate was collected

Sources & evidence

ORD record
ord-dab07e4db9e64dd9be9bb3ca634656f7
Source dataset
uspto-grants-2015_04
Patent number
US09012470B2

Reaction notes

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