3-(Trifluoromethyl)benzoyl chloride → N-[3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzooxazol-6-yl}oxy)phenyl]-3-(trifluoromethyl)benzamide

HRID 2190488ノート

反応式

HRID 2190488 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:20]=[CH:19][C:9]2[N:10]=[C:11]([NH:13][C:14]([CH:16]3[CH2:18][CH2:17]3)=[O:15])[O:12][C:8]=2[CH:7]=1.[F:24][C:25]([F:36])([F:35])[C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](Cl)=[O:30]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH:16]1([C:14]([NH:13][C:11]2[O:12][C:8]3[CH:7]=[C:6]([O:5][C:4]4[CH:3]=[C:2]([NH:1][C:29](=[O:30])[C:28]5[CH:32]=[CH:33][CH:34]=[C:26]([C:25]([F:24])([F:35])[F:36])[CH:27]=5)[CH:23]=[CH:22][CH:21]=4)[CH:20]=[CH:19][C:9]=3[N:10]=2)=[O:15])[CH2:18][CH2:17]1

参加物

5

反応物 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 67312021N-[6-(3-aminophenoxy)-1,3-benzooxazol-2-yl]cyclopropanecarboxamide

生成物 1

HCID 58349060N-[3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzooxazol-6-yl}oxy)phenyl]-3-(trifluoromethyl)benzamide収率 50%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒2 回

実験手順

To a solution of N-[6-(3-aminophenoxy)-1,3-benzooxazol-2-yl]cyclopropanecarboxamide (128 mg, 415 μmol) in pyridine (3 mL) were added a solution of 3-(trifluoromethyl)benzoyl chloride prepared above in pyridine (2 mL) and N,N-dimethylpyridine-4-amine (58.9 mg, 482 μmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methanol (10 mL) and ethyl acetate (100 mL). This solution was washed with 0.1N hydrochloric acid (50 mL) and saturated aqueous sodium hydrogencarbonate solution (50 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/98→80/20) to give the title compound (101 mg, 50%) as a colorless solid.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in methanol (10 mL)
  3. washThis solution was washed with 0.1N hydrochloric acid (50 mL) and saturated aqueous sodium hydrogencarbonate solution (50 mL)
  4. dry with materialsuccessively, and dried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/98→80/20)

出典と根拠

ORDレコード
ord-904b04281569424ebfbbf802f0ed7cf4
出典データセット
uspto-grants-2012_12
特許番号
US08324395B2

反応ノート

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