四氢呋喃 → Methyl 2-(3-(4-(3-(2,4-difluorophenyl) ureido)phenyl)-1,2,4-oxadiazole-5-carboxamido)-3-methylbutanoate

HRID 75813笔记

反应方程式

HRID 75813 反应方程式
[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

参与物

5

反应物 3

HCID 8028四氢呋喃HCID 5932582,4-二氟苯基异氰酸酯HCID 67353979Methyl 2-(3-(4-aminophenyl)-1,2,4-oxadiazole-5-carboxamido)-3 methylbutanoate

产物 1

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

试剂、催化剂与溶剂 1

HCID 8857乙酸乙酯溶剂

实验过程

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).

后处理

  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%

来源与证据

ORD记录
ord-e70e7a9544f14932bbe8fdf59c660372
来源数据集
uspto-grants-2014_09
专利号
US08835428B2

反应笔记

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