HCID 66749622, compound → HCID 56839793, compound

HRID 537055Notes

Reaction equation

HRID 537055 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:12][C:13]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])=[C:14]([C:16]([NH:18][CH2:19][CH:20]([O:23]C)OC)=O)[N:15]=2)[C:8]([CH3:32])=[CH:7][N:6]=1)(=[O:3])[CH3:2].CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O>[Cl:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:13]1[O:12][C:11]([C:9]2[C:8]([CH3:32])=[CH:7][N:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=2)=[N:15][C:14]=1[C:16]1[O:23][CH:20]=[CH:19][N:18]=1

Participants

4

Reactant 2

HCID 66749622HCID 66749622, compoundHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 56839793HCID 56839793, compoundYield 2.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-(2-acetamido-5-methylpyridin-4-yl)-5-(2-chlorophenyl)-N-(2,2-dimethoxyethyl)-1,3-oxazole-4-carboxamide (0.226 g, 0.492 mmol) and Eaton's Reagent (7.7 wt % phosphorus pentoxide solution in methanesulfonic acid, 1.2 mL) was allowed to stir at 130° C. for 3 hr. Water was added to the reaction mixture and the solution was extracted with EtOAc. The organic solutions were combined, washed with brine and aqueous sat. NaHCO3, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give N-{4-[5′-(2-chlorophenyl)-2,4′-bi-1,3-oxazol-2′-yl]-5-methylpyridin-2-yl}acetamide (Compound I-10) (0.005 g, 2%). LCMS (FA): m/z=395 (M+H).

Workup

  1. extractionthe solution was extracted with EtOAc
  2. washwashed with brine and aqueous sat. NaHCO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-06c79cb1afb447978ce5807ac7339527
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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