Tetrahydrofuran → Methyl 2-(3-(4-(3-(2,4-difluorophenyl) ureido)phenyl)-1,2,4-oxadiazole-5-carboxamido)-3-methylbutanoate

HRID 75813

Reaction equation

HRID 75813 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]([NH:15][CH:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])=[O:14])[O:10][N:9]=2)=[CH:4][CH:3]=1.[F:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[N:32]=[C:33]=[O:34].C1COCC1>C(OCC)(=O)C>[F:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[NH:32][C:33](=[O:34])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]([NH:15][CH:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])=[O:14])[O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 5932582,4-Difluorophenyl isocyanateHCID 67353979Methyl 2-(3-(4-aminophenyl)-1,2,4-oxadiazole-5-carboxamido)-3 methylbutanoate

Product 1

HCID 67354586Methyl 2-(3-(4-(3-(2,4-difluorophenyl) ureido)phenyl)-1,2,4-oxadiazole-5-carboxamido)-3-methylbutanoateYield 98.65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-(3-(4-aminophenyl)-1,2,4-oxadiazole-5-carboxamido)-3 methylbutanoate and 2,4-difluoro-1-isocyanatobenzene was added to THF and stirred at room temperature overnight. After completion of the reaction, the solvent was evaporated and the crude product so obtained was dissolved in ethyl acetate and washed with water, brine, dried by sodium sulfate and concentrated to give a solid. The solid was re-crystallized from Ethyl acetate: Pet ether and was obtained in a yield of 98.65%; 1H NMR (DMSO-d6) δ: 0.970 (t, 6H C(CH3)2), 2.488 (m, 1H, CHMe2), 3.68 (s, 3H, OCH3), 4.35 (m, 1H, NHCH), 7.082 (m, 1H CH), 7.35 (m, 1H, CH), 7.67 (d, 2H, CH) 8.011 (d, 2H CH), 8.099 (m, 1H, CH), 8.96 (s, 1H, NH), 9.384 (s, 1H, NH), 9.677 (d, 1H, NH); ms (m/z) 474 (M++H).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. customthe crude product so obtained
  4. washwashed with water, brine
  5. dry with materialdried by sodium sulfate
  6. concentrationconcentrated
  7. customto give a solid
  8. customThe solid was re-crystallized from Ethyl acetate
  9. customPet ether and was obtained in a yield of 98.65%

Sources & evidence

ORD record
ord-e70e7a9544f14932bbe8fdf59c660372
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Linked notes

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