HCID 59853014, compound → HCID 59852861, compound

HRID 1670287Notes

Reaction equation

HRID 1670287 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18]C(=O)OC(C)(C)C)=[CH:14][C:13]=2[F:26])[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]>Cl.O1CCOCC1.CCOC(C)=O.C([O-])(O)=O.[Na+]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:9]2[CH:8]=[CH:7][N:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=2)=[C:13]([F:26])[CH:14]=1

Participants

5

Reactant 1

HCID 59853014HCID 59853014, compound

Product 1

HCID 59852861HCID 59852861, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolventHCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of tert-butyl 4-(2-acetamidopyridin-4-yloxy)-3-fluorophenylcarbamate (110 mg, 0.30 mmol) in 4 M HCl/1,4-dioxane (1.5 mL) was stirred at 0° C. for 20 min then at room temperature for 25 min. The mixture was diluted with EtOAc (25 mL) and saturated aq. NaHCO3 solution (20 mL), and stirred vigorously for 5 min. The EtOAc phase was washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound (69 mg, 87%) as a yellow solid. 1H NMR (DMSO-d6) δ 10.49 (s, 1H), 8.13 (d, 1H, J=5.6 Hz), 7.60 (m, 1H), 6.95 (dd, 1H, J=8.6, 9.2 Hz), 6.60 (dd, 1H, J=2.5, 5.6 Hz), 6.48 (dd, 1H, J=2.5, 13.2 Hz), 6.40 (dd, 1H, J=2.0, 8.6 Hz), 5.44 (s, 2H), 2.02 (s, 3H).

Workup

  1. washThe EtOAc phase was washed with brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b4e9c6d439654deb9c0ca23f31d1dc62
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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