Hydrochloric Acid → HCID 11558501, compound

HRID 2377084Notes

Reaction equation

HRID 2377084 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:17](OC)=[O:18])[C:15]([OH:16])=[C:10]3[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[NH2:23][OH:24].[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:17]([NH:23][OH:24])=[O:18])[C:15]([OH:16])=[C:10]3[CH:9]=[CH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 53237467methyl 1-(4-fluorobenzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylate

Product 1

HCID 11558501HCID 11558501, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl 1-(4-fluorobenzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (0.22 g, 0.73 mmol) in methanol (10 mL) were added hydroxylamine (2 mL, 30.3 mmol, 50% in water) and sodium hydroxide (2.0 mL. 2.0 mmol, 1 N aqueous solution). The resulting solution was stirred for 16 h at ambient temperature. After addition of 1N hydrochloric acid (2.0 mL. 2.0 mmol) the product precipitated out. It was collected by filtration, washed with water and ethyl acetate, and dried in vacuo to provide the title compound as a solid (0.18 g, 82% yield). 1H NMR (DMSO-d6) δ: 13.19 (s, 1H), 11.41 (s, 1H), 9.17 (s, 1H), 8.39 (s, 1H), 7.71 (d, 1H, 7.34 (t, 2H, 7.16 (t, 2H) 6.68 (d, 1H), 5.54 (s, 2H). LCMS (APCI, M+H+): 302.1. HRMS calcd for C15H12FN3O3 (M+H) 302.0936, found 302.0935. HPLC: 100% purity.

Workup

  1. customprecipitated out
  2. filtrationIt was collected by filtration
  3. washwashed with water and ethyl acetate
  4. customdried in vacuo

Sources & evidence

ORD record
ord-0a64a4b8d9cf42d183cba255bee79275
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

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