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

HRID 75813

反応式

HRID 75813 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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%

出典と根拠

ORDレコード
ord-e70e7a9544f14932bbe8fdf59c660372
出典データセット
uspto-grants-2014_09
特許番号
US08835428B2

関連ノート

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