Ethyl Acetate → 4-Acetamido-N-(2-amino-5-(benzo[d]oxazol-2-yl)phenyl)benzamide

HRID 252845

反応式

HRID 252845 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[C:12]([NH2:17])[C:13]([NH2:16])=[CH:14][CH:15]=1.[C:18]([NH:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)(=[O:20])[CH3:19].CCOC(C)=O>C(#N)C.N1C=CC=CC=1>[C:18]([NH:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:17][C:12]2[CH:11]=[C:10]([C:2]3[O:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)[CH:15]=[CH:14][C:13]=2[NH2:16])=[O:27])=[CH:24][CH:23]=1)(=[O:20])[CH3:19]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 70103414-Acetamidobenzoyl chlorideHCID 146378974-(Benzo[d]oxazol-2-yl)benzene-1,2-diamine

生成物 1

HCID 597367264-Acetamido-N-(2-amino-5-(benzo[d]oxazol-2-yl)phenyl)benzamide収率 1%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6342Acetonitrile溶媒2 回

実験手順

To a stirred suspension of 227 (350 mg, 1.55 mmol) in acetonitrile (20 mL) and pyridine (2 ml) was added 4-acetamidobenzoyl chloride (307 mg, 1.55 mmol) in acetonitrile (5 ml) at 0° C. The solution was warmed up to room temperature and stirred for 4 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel, eluents hexane-EtOAc (1:3), then EtOAc (100%), to afford 228 as a beige solid (5 mg, 1% yield). 1H NMR: (DMSO) δ (ppm): 10.22 (s, 1H), 9.62 (s, 1H), 8.05 (d, J=2.4 Hz, 1H), 7.89 (d, J=8.4 Hz, 2H), 7.80 (1H, dd, J=2.0, 8.4 Hz, 1H), 7.68-7.73 (m, 4H), 7.33-7.35 (m, 2H), 6.91 (d, J=8.4 Hz, 1H), 5.86 (bs, 2H), 2.12 (s, 3H). MS: (calc.) 386.41; (obt.) 387.1 (MH)+.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel, eluents hexane-EtOAc (1:3)

出典と根拠

ORDレコード
ord-79fc891a262542d0af8b5159917f61bc
出典データセット
uspto-grants-2011_01
特許番号
US07868205B2

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