HCID 58360247, compound → HCID 44540665, compound

HRID 402577Notes

Reaction equation

HRID 402577 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][CH2:7][C:8]2[CH:13]=[N:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[C:10]3[O:18]C(C)(C)[O:20][CH2:21][C:9]=23)=[CH:4][CH:3]=1>C(O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]2[C:9]([CH2:21][OH:20])=[C:10]([OH:18])[C:11]([C:14]([O:16][CH3:17])=[O:15])=[N:12][CH:13]=2)=[CH:24][CH:25]=1

Participants

3

Reactant 1

HCID 58360247HCID 58360247, compound

Product 1

HCID 44540665HCID 44540665, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of methyl 5-((4-fluorophenoxy)methyl)-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylate 28a (0.129 g, 0.37 mmol) in 3 mL of formic acid was stirred at 23° C. for 2 h and then it was concentrated. The crude residue was purified by chromatography (SiO2) with hexanes:ethyl acetate (3:7) as eluent to afford the title compound as a white solid: LC-MS (M+H)+ m/z 308; 1H NMR (DMSO-d6): 1.39 (s, 6H), 4.80 (s, 2H), 4.89 (s, 2H), 5.01 (s, 2H), 7.39-7.46 (m, 5H), 8.38 (s, 1H), 10.04 (s, 1H).

Workup

  1. concentrationit was concentrated
  2. customThe crude residue was purified by chromatography (SiO2) with hexanes:ethyl acetate (3:7) as eluent

Sources & evidence

ORD record
ord-4594d361e595458eb381e853c595ccd2
Source dataset
uspto-grants-2014_06
Patent number
US08742123B2

Reaction notes

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