1,1'-Carbonyldiimidazole → HCID 86666248, compound

HRID 537051Notes

Reaction equation

HRID 537051 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:12][C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])=[C:14]([C:16](O)=[O:17])[N:15]=2)[C:8]([CH3:26])=[CH:7][N:6]=1)(=[O:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:40][O:41][NH:42][CH3:43]>C(Cl)Cl.O>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:12][C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])=[C:14]([C:16]([N:42]([O:41][CH3:40])[CH3:43])=[O:17])[N:15]=2)[C:8]([CH3:26])=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 66749149HCID 66749149, compound

Product 1

HCID 86666248HCID 86666248, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-acetamido-5-methylpyridin-4-yl)-5-(2-chlorophenyl)-1,3-oxazole-4-carboxylic acid (0.303 g, 0.815 mmol) in DCM (2 mL) was added CDI (0.14 g, 0.87 mmol). The reaction mixture was allowed to stir at rt for 30 min, then at reflux for 30 min. The reaction mixture was allowed to cool to rt and TEA (0.125 mL, 0.896 mmol) and N-methoxymethanamine hydrochloride (0.835 g. 0.856 mmol) were added. The reaction mixture was allowed to stir at rt overnight and then diluted with water. The aqueous solution was separated and extracted with DCM. The organic solutions were combined, washed sequentially with 10% citric acid, saturated aq. NaHCO3 (50 mL) and brine, dried over Na2SO4, filtered and concentrated to give 2-(2-acetamido-5-methylpyridin-4-yl)-5-(2-chlorophenyl)-N-methoxy-N-methyl-1,3-oxazole-4-carboxamide (0.187 g, 55%), which was used without purification in the next step. LCMS (FA): m/z=415.4 (M+H).

Workup

  1. temperatureat reflux for 30 min
  2. temperatureto cool to rt
  3. stirringto stir at rt overnight
  4. customThe aqueous solution was separated
  5. extractionextracted with DCM
  6. washwashed sequentially with 10% citric acid, saturated aq. NaHCO3 (50 mL) and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-73accb1896024f86bd2dc8446203b343
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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