Sodium Hydroxide → HCID 67351907, compound

HRID 1672828Notes

Reaction equation

HRID 1672828 reaction equation
[C:1]([C:3]1[O:7][C:6]([C:8]2[CH:9]=[C:10]([N:14]3[CH2:23][C@H:22]4[N:18]([CH2:19][CH2:20][CH2:21]4)[C:17]4[N:24]=[C:25]([S:28][CH3:29])[N:26]=[CH:27][C:16]=4[C:15]3=[O:30])[CH:11]=[CH:12][CH:13]=2)=[N:5][CH:4]=1)#[N:2].[OH-:31].[Na+]>C(O)C.C(OCC)(=O)C>[CH3:29][S:28][C:25]1[N:26]=[CH:27][C:16]2[C:15](=[O:30])[N:14]([C:10]3[CH:9]=[C:8]([C:6]4[O:7][C:3]([C:1]([NH2:2])=[O:31])=[CH:4][N:5]=4)[CH:13]=[CH:12][CH:11]=3)[CH2:23][C@H:22]3[N:18]([CH2:19][CH2:20][CH2:21]3)[C:17]=2[N:24]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67350395HCID 67350395, compound

Product 1

HCID 67351907HCID 67351907, compoundYield 34.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-5-[3-(5-Cyano-1,3-oxazol-2-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (140 mg, 0.334 mmol) obtained in Step 3 of Example 125 was dissolved in ethanol (5 mL), and the mixture was stirred at room temperature for 2 hours after adding a 2 mol/L aqueous sodium hydroxide solution (1.67 mL, 3.34 mmol). The mixture was diluted with ethyl acetate, and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give (S)-2-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,3-oxazole-5-carboxamide (50.3 mg, 34%).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-53f32572f3024e819a782f4a4b7b4fcd
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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