Sodium Hydroxide → HCID 86271488, compound

HRID 528004Notes

Reaction equation

HRID 528004 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:34][CH3:35])=[C:6]([C:8]2[C:9]3[CH:16]=[C:15]([C:17]4[CH2:18][CH2:19][N:20]([CH2:23][C:24]5[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=5)[CH2:21][CH:22]=4)[NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:7]=1.[OH-].[Na+]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:34][CH3:35])=[C:6]([C:8]2[C:9]3[CH:16]=[C:15]([C:17]4[CH2:18][CH2:19][N:20]([CH2:23][C:24]5[CH:25]=[CH:26][C:27]([C:28]([OH:30])=[O:29])=[CH:32][CH:33]=5)[CH2:21][CH:22]=4)[NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86271392HCID 86271392, compound

Product 1

HCID 86271488HCID 86271488, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of Example 71 (60 mg, 0.127 mmol) in 5 mL dioxane was added 6 M sodium hydroxide (212 μL, 1.270 mmol). The reaction mixture was held at 50° C. for 12 hours and then diluted with 25 mL water. The aqueous mixture was extracted with ethyl acetate (2×), and the organic fractions were discarded. The aqueous layer was diluted with an equal amount of ethyl acetate and made slightly acidic with 2.5 M hydrochloric acid. The aqueous layer was extracted with ethyl acetate (2×), and the combined organic fractions were washed with brine, dried over magnesium sulfate and concentrated to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 12.20 (s, 1H) 8.76 (s, 1H) 7.92 (d, J=7.93 Hz, 2H) 7.47 (d, J=8.24 Hz, 2H) 7.28-7.39 (m, 2H) 7.15-7.27 (m, 1H) 6.54 (s, 1H) 6.28 (d, J=1.53 Hz, 1H) 3.78 (s, 3H) 3.68 (s, 2H) 3.14 (s, 2H) 2.65 (t, J=5.49 Hz, 2H) 2.50 (s, 3H). MS (ESI+) m/z 459.1 (M+H)+.

Workup

  1. extractionThe aqueous mixture was extracted with ethyl acetate (2×)
  2. additionThe aqueous layer was diluted with an equal amount of ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×)
  4. washthe combined organic fractions were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-23bf2fddefaf477d9a4fc56da104badc
Source dataset
uspto-grants-2016_05
Patent number
US09346813B2

Reaction notes

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