Ammonia → HCID 66749242, compound

HRID 537072Notes

Reaction equation

HRID 537072 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:12][C:13]([C:17](O)=[O:18])=[C:14]([I:16])[N:15]=2)[C:8]([CH3:20])=[CH:7][N:6]=1)(=[O:3])[CH3:2].C(Cl)(=O)OCC(C)C.[NH3:29]>C1COCC1.O>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:12][C:13]([C:17]([NH2:29])=[O:18])=[C:14]([I:16])[N:15]=2)[C:8]([CH3:20])=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 62365Isobutyl chloroformateHCID 66749337HCID 66749337, compound

Product 1

HCID 66749242HCID 66749242, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2-(2-acetamido-5-methylpyridin-4-yl)-4-iodo-1,3-oxazole-5-carboxylic acid (10.0 g, 26 mmol) in THF (200 mL) was added TEA (11.0 mL, 78.0 mmol). The reaction mixture was allowed to stir at rt for 1 h and then isobutyl carbonochloridate (10.0 mL, 74.0 mmol) was added. The reaction mixture was allowed to stir at rt for 5 hr and then saturated ammonia in THF (100 mL) was added. The reaction mixture was allowed to stir at rt for 30 min and was then diluted with water. The organic solvent was removed by evaporation and the slurry was filtered. The solid was collected, washed with water and dried to give 2-(2-acetamido-5-methylpyridin-4-yl)-4-iodo-1,3-oxazole-5-carboxamide (8.7 g, 87%).

Workup

  1. stirringto stir at rt for 5 hr
  2. stirringto stir at rt for 30 min
  3. customThe organic solvent was removed by evaporation
  4. filtrationthe slurry was filtered
  5. customThe solid was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-32cabed5019948abb0e0a29e47f15602
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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