Sodium Hydroxide → HCID 58337739, compound

HRID 1887441Notes

Reaction equation

HRID 1887441 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:15]C(=O)OC(C)(C)C)[CH:5]=[C:6]([O:8][C:9]2[CH:10]=[N:11][CH:12]=[N:13][CH:14]=2)[CH:7]=1.[OH-].[Na+]>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([O:8][C:9]2[CH:14]=[N:13][CH:12]=[N:11][CH:10]=2)[CH:7]=1)[NH2:15]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58337569HCID 58337569, compound

Product 1

HCID 58337739HCID 58337739, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound 8 (48 mg, 0.15 mmol, 1.0 eq) was dissolved in 4N HCl in dioxane (0.75 mL) and stirred at room temperature until determination of completion by TLC. The reaction was neutralized with 1N NaOH and extracted with EtOAc (3×). The combined organics were dried (MgSO4), filtered and concentrated in vacuo to give 29 mg (88%) of an orange solid: 1H NMR (400 MHz, DMSO-d6) δ 9.03 (s, 1H), 8.67 (s, 2H), 6.55 (s, 1H), 6.42 (s, 1H), 6.30 (s, 1H); ES-MS [M+1]+: 222.0.

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d9b60621d1e4c63945a371ef9fec727
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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