Diisopropylethylamine → 2-(2,6-Dichlorophenyl)-benzooxazole-6-carboxylic acid (2-o-tolyl-ethyl)-amide

HRID 1514971ノート

反応式

HRID 1514971 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[O:10][C:11]2[CH:17]=[C:16]([C:18]([OH:20])=O)[CH:15]=[CH:14][C:12]=2[N:13]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[C:57]1([CH3:66])[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[CH2:63][CH2:64][NH2:65]>CN(C=O)C>[C:57]1([CH3:66])[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[CH2:63][CH2:64][NH:65][C:18]([C:16]1[CH:15]=[CH:14][C:12]2[N:13]=[C:9]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])[O:10][C:11]=2[CH:17]=1)=[O:20]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 20638682-MethylphenethylamineHCID 53271602-(2,6-Dichlorophenyl)-1,3-benzoxazole-6-carboxylic acid

生成物 1

HCID 251092472-(2,6-Dichlorophenyl)-benzooxazole-6-carboxylic acid (2-o-tolyl-ethyl)-amide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

To a solution of 2-(2,6-dichloro-phenyl)-benzooxazole-6-carboxylic acid (8.9 mg) in anhydrous DMF (0.5 mL) was added BOP (17.4 mg), diisopropylethylamine (0.014 mL), and 2-o-tolyl-ethylamine (5.5 mg). The reaction mixture was stirred at 85° C. overnight, quenched with 1N NaOH aqueous solution at 0° C., extracted with EtOAc. The extracts were dried over Na2SO4 and concentrated in vacuo. The crude reaction mixture was purified by silica SPE eluting with EtOAc/Hexane to give 2-(2,6-dichlorophenyl)-benzooxazole-6-carboxylic acid (2-o-tolyl-ethyl)-amide: MS (m/z) 425.1 (M+1).

後処理

  1. customquenched with 1N NaOH aqueous solution at 0° C.
  2. extractionextracted with EtOAc
  3. dry with materialThe extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude reaction mixture
  6. customwas purified by silica SPE
  7. washeluting with EtOAc/Hexane

出典と根拠

ORDレコード
ord-82076be12c4449a286c95c20edd76664
出典データセット
uspto-grants-2012_07
特許番号
US08222248B2

反応ノート

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