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

HRID 1514971노트

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HRID 1514971 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-82076be12c4449a286c95c20edd76664
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222248B2

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