Hydrochloric Acid → HCID 90050662, compound

HRID 931381Notes

Reaction equation

HRID 931381 reaction equation
[F:1][C:2]1([F:24])[C:10]2([C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]2=[O:19])[CH2:9][C:8]2[C:3]1=[CH:4][C:5]([C:20]([O:22]C)=[O:21])=[CH:6][CH:7]=2.[OH-].[Na+].Cl>CO>[F:24][C:2]1([F:1])[C:10]2([C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]2=[O:19])[CH2:9][C:8]2[C:3]1=[CH:4][C:5]([C:20]([OH:22])=[O:21])=[CH:6][CH:7]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 118023175HCID 118023175, compound

Product 1

HCID 90050662HCID 90050662, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 1,1-difluoro-2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridine]-6-carboxylate (100 mg, 0.30 mmol) and aqueous 6 N sodium hydroxide solution (0.15 mL, 0.91 mmol) in MeOH (5 mL) is heated at reflux for 1 h. The mixture is allowed to cool to ambient temperature before it is acidified to pH ˜6 with aqueous 1 N hydrochloric acid solution. The resulting mixture is filtered, and the filtrate is concentrated. The residue is partitioned between water (10 mL) and 2-methyltetrahydrofuran (2-MeTHF, 10 mL). The aqueous layer is extracted with 2-MeTHF (5×10 mL), and the combined organic layers are dried over sodium sulfate and concentrated in vacuo to provide the title compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 h
  3. filtrationThe resulting mixture is filtered
  4. concentrationthe filtrate is concentrated
  5. customThe residue is partitioned between water (10 mL) and 2-methyltetrahydrofuran (2-MeTHF, 10 mL)
  6. extractionThe aqueous layer is extracted with 2-MeTHF (5×10 mL)
  7. dry with materialthe combined organic layers are dried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d86cc8804f204b4eb7f111049a5f043f
Source dataset
uspto-grants-2016_03
Patent number
US09296750B2

Reaction notes

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