Cyclopropanecarbonyl chloride → 3-(1-cyanocyclopropyl)-N-[5-({2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazol-6-yl}oxy)-2-methylphenyl]benzamide

HRID 2190371ノート

反応式

HRID 2190371 の反応式
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[CH:14][C:15]([CH3:32])=[C:16]([NH:18][C:19](=[O:31])[C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]5([C:29]#[N:30])[CH2:28][CH2:27]5)[CH:21]=4)[CH:17]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1>CN(C)C(=O)C.C(OCC)(=O)C>[C:29]([C:26]1([C:22]2[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=2)[C:19]([NH:18][C:16]2[CH:17]=[C:12]([O:11][C:9]3[CH:8]=[CH:7][C:5]4[N:6]=[C:2]([NH:1][C:36]([CH:33]5[CH2:35][CH2:34]5)=[O:37])[S:3][C:4]=4[CH:10]=3)[CH:13]=[CH:14][C:15]=2[CH3:32])=[O:31])[CH2:27][CH2:28]1)#[N:30]

参加物

5

反応物 2

HCID 77637Cyclopropanecarbonyl chloride2 回HCID 86655351N-{5-[(2-amino-1,3-benzothiazol-6-yl)oxy]-2-methylphenyl}-3-(1-cyanocyclopropyl)benzamide

生成物 1

HCID 866553523-(1-cyanocyclopropyl)-N-[5-({2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazol-6-yl}oxy)-2-methylphenyl]benzamide収率 40.4%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

実験手順

To a solution of N-{5-[(2-amino-1,3-benzothiazol-6-yl)oxy]-2-methylphenyl}-3-(1-cyanocyclopropyl)benzamide (300 mg, 0.681 mmol) in N,N-dimethylacetamide (3.0 mL) was added cyclopropanecarbonyl chloride (65 μL, 0.715 mmol), and the mixture was stirred at room temperature for 10 hr. To the reaction mixture was added cyclopropanecarbonyl chloride (30 μL, 0.33 mmol), and the mixture was further stirred at room temperature for 3 hr. The reaction mixture was diluted with ethyl acetate (100 mL), washed with 5% aqueous sodium hydrogencarbonate solution (100 mL) and saturated brine (100 mL), successively, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30→0/100), and the obtained solution was concentrated under reduced pressure. The residue was triturated with ethyl acetate/diisopropyl ether to give the title compound (140 mg, 40%) as a colorless solid.

後処理

  1. stirringthe mixture was further stirred at room temperature for 3 hr
  2. washwashed with 5% aqueous sodium hydrogencarbonate solution (100 mL) and saturated brine (100 mL)
  3. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30→0/100)
  7. concentrationthe obtained solution was concentrated under reduced pressure
  8. customThe residue was triturated with ethyl acetate/diisopropyl ether

出典と根拠

ORDレコード
ord-4dee86f65db54da0953aee91cea0607a
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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