Sodium Hydroxide → HCID 58934590, compound

HRID 854968Notes

Reaction equation

HRID 854968 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([CH3:25])([CH3:24])[CH2:13][NH:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[O:8][CH:7]([C:26]([F:29])([F:28])[F:27])[C:6]([C:30]([O:32]CC)=[O:31])=[CH:5]2.[OH-].[Na+]>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([CH3:25])([CH3:24])[CH2:13][NH:14][C:15](=[O:23])[C:16]1[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=1)[O:8][CH:7]([C:26]([F:28])([F:29])[F:27])[C:6]([C:30]([OH:32])=[O:31])=[CH:5]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69517098HCID 69517098, compound

Product 1

HCID 58934590HCID 58934590, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The title product of Example 130 Step 2 was dissolved in 5 mL of MeOH, and a solution of 244 mg of 50% aqueous NaOH in 1 mL of water was added. After stirring for 2 h, the mixture was acidified, extracted with DCM, the combined organic extracts dried over Na2SO4, filtered, and evaporated. Chromatography of the residue over silica gel using 25% EtOAc—heptane—1% HOAc gave the title compound, 65 mg, as a pure white crystalline solid. 1H NMR (DMSO-d6) 8.34 (t, 1H, J=4.6 Hz), 7.86 (s, 1H), 7.72 (d, 2H, J=8.8 Hz), 7.60 (s, 1H), 7.48 (d, 2H, J=8.8Hz), 7.03 (s, 1H), 5.93 (q, 1H, J=7.2 Hz), 3.78 (m, 2H), 1.44 (s, 6H). LCMS m/z=488.0.

Workup

  1. extractionextracted with DCM
  2. dry with materialthe combined organic extracts dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-30f8c96783c5474f981a4b87b16a5ab3
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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