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

HRID 75813

반응식

HRID 75813 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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%

출처 및 근거

ORD 기록
ord-e70e7a9544f14932bbe8fdf59c660372
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835428B2

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