Sodium Hydroxide → HCID 87191657, compound

HRID 2089032Notes

Reaction equation

HRID 2089032 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([OH:17])[CH:15]=3)[N:10](S(C3C=CC=CC=3)(=O)=O)[CH:9]=2)[CH:5]=[C:4]([NH:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[N:3]=1.[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([OH:17])[CH:15]=3)[NH:10][CH:9]=2)[CH:5]=[C:4]([NH:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 87191995HCID 87191995, compound

Product 1

HCID 87191657HCID 87191657, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of Example 180a (80.0 mg, 0.166 mmol) in dioxane (2 mL) was treated with 20% NaOH (0.20 mL). The reaction was heated at 90° C. for 2 hours. The solvent was evaporated. The residue was dissolved in water, neutralized with trifluoroacetic acid, treated with DMSO/MeOH, and purified by reverse-phase HPLC as described in Example 56 to give the title compound (40.2 mg) as trifluoroacetic acid salts. 1H NMR (500 MHz, CD3OD) ppm 1.30 (q, J=12.51 Hz, 3H), 1.39-1.56 (m, 2H), 1.69 (m, 1H), 1.75-1.86 (m, 2H), 2.04 (dd, J=12.51, 3.36 Hz, 2H), 3.72 (m, 1H), 6.76 (d, J=1.22 Hz, 1H), 6.90 (d, J=1.22 Hz, 1H), 7.84 (d, J=2.44 Hz, 1H), 7.91 (s, 1H), 7.97 (s, 1H). MS (DCI+) m/z 343.2 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in water
  3. additiontreated with DMSO/MeOH
  4. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-6d7f81e4aaae47ce86b24137be2e3cae
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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