Tris(hydroxymethyl)aminomethane → N-{3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenyl}-isobutyramide

HRID 2101521ノート

反応式

HRID 2101521 の反応式
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[Cl:7][C:8]1[CH:9]=[C:10]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH2:17][O:18][C:19]1[CH:20]=[C:21]([NH2:25])[CH:22]=[CH:23][CH:24]=1.C(O)C(N)(CO)CO>C(Cl)Cl>[Cl:7][C:8]1[CH:9]=[C:10]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH2:17][O:18][C:19]1[CH:20]=[C:21]([NH:25][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[CH:22]=[CH:23][CH:24]=1

参加物

5

反応物 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 62325Isobutyryl chlorideHCID 119510703-[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenylamine

生成物 1

HCID 11951240N-{3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenyl}-isobutyramide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Isobutyryl chloride (11 mg, 0.1 mmol) was added to a solution of 3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenylamine (see Example 21) (30 mg, 0.09 mmol) in CH2Cl2 (1 mL). The reaction was shaken at room temperature. After 72 h, trisamine resin (79 mg, 0.1 mmol) was added and the reaction was shaken for another 4 h. The reaction was filtered and the resin was washed with CH2Cl2 (2 mL). The filtrates were combined and concentrated in vacuo. Preparative TLC (silica, 20:1 CH2Cl2:MeOH, Rf=0.4) provided N-{3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenyl}-isobutyramide, 24a as a white solid (15 mg, 40%); MS m/z 418 [C21H21Cl2N3O2+H]+.

後処理

  1. stirringthe reaction was shaken for another 4 h
  2. filtrationThe reaction was filtered
  3. washthe resin was washed with CH2Cl2 (2 mL)
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7c7825d9b33d41ffa86333fdcfeff637
出典データセット
uspto-grants-2009_08
特許番号
US07572921B2

反応ノート

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