Ammonia → 2-Iodo-5-(4-methoxyphenyl)oxazole-4-carboxamide

HRID 714973Notes

Reaction equation

HRID 714973 reaction equation
[I:1][C:2]1[O:3][C:4]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:5]([C:7](O)=[O:8])[N:6]=1.O.OC1C2N=N[NH:25]C=2C=CC=1.N.O1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[I:1][C:2]1[O:3][C:4]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:5]([C:7]([NH2:25])=[O:8])[N:6]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 685208722-Iodo-5-(4-methoxyphenyl)oxazole-4-carboxylic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 685209522-Iodo-5-(4-methoxyphenyl)oxazole-4-carboxamideYield 70.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution 2-iodo-5-(4-methoxyphenyl)oxazole-4-carboxylic acid (0.92 g, 2.7 mmol) in DCM (20 mL) and DMF (10 mL) was added hydroxybenzotriazole monohydrate (0.44 g, 2.9 mmol) followed by 0.5M ammonia in dioxane (22 mL, 11.0 mmol) and 1-(3-(dimethylamino)propyl)-3-ethyl-carbodiimide hydrochloride (0.77 g, 4.0 mmol) and the reaction stirred at room temperature overnight. EtOAc was then added and the mixture washed with brine. The organic phase was dried over MgSO4 and the solvent removed in vacuo. The residue was purified by silica gel column chromatography using gradient of 0-50% EtOAc in DCM to afford 2-iodo-5-(4-methoxyphenyl)oxazole-4-carboxamide (0.66 g. 1.9 mmol, 70%) as a yellow solid. 1H NMR (CDCl3) 3.79 (3H, s), 5.47 (1H, br. s), 6.90 (2H, d), 6.94 (1H, br. s), 8.14 (2H, d). LCMS (1) Rt: 1.84 min; m/z (ES+) 345.

Workup

  1. washthe mixture washed with brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9ee01b053e0f4e4d935346588c0849e6
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Reaction notes

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