Ethanol → N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]phenyl}-3-(trifluoromethyl)benzamide

HRID 1874580ノート

反応式

HRID 1874580 の反応式
Cl.NO.C([N:7](CC)C(C)C)(C)C.C(O)C.[F:16][C:17]([F:50])([F:49])[C:18]1[CH:19]=[C:20]([CH:46]=[CH:47][CH:48]=1)[C:21]([NH:23][C:24]1[CH:25]=[C:26]([CH:43]=[CH:44][CH:45]=1)[O:27][C:28]1[CH:29]=[CH:30][C:31]([NH:34][C:35]([NH:37]C(=O)OCC)=S)=[N:32][CH:33]=1)=[O:22]>CO>[NH2:37][C:35]1[N:34]=[C:31]2[CH:30]=[CH:29][C:28]([O:27][C:26]3[CH:25]=[C:24]([NH:23][C:21](=[O:22])[C:20]4[CH:46]=[CH:47][CH:48]=[C:18]([C:17]([F:16])([F:49])[F:50])[CH:19]=4)[CH:45]=[CH:44][CH:43]=3)=[CH:33][N:32]2[N:7]=1

参加物

6

反応物 4

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 86631984Ethyl ({[5-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)pyridin-2-yl]amino}carbonothioyl)carbamate

生成物 1

HCID 68416765N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]phenyl}-3-(trifluoromethyl)benzamide収率 122.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of hydroxylamine hydrochloride (400 mg, 5.76 mmol) and N,N-diisopropylethylamine (1.20 mL, 6.88 mmol) in methanol (8.0 mL)/ethanol (8.0 mL) was added ethyl ({[5-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)pyridin-2-yl]amino}carbonothioyl)carbamate (480 mg, 0.95 mmol) obtained above, and the mixture was stirred with heating at 60° C. for 12 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate (100 mL). The mixture was washed with water (50 mL) and saturated brine (50 mL), 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=50/50→0/100), and fractions containing the desired product were concentrated under reduced pressure to give the title compound (0.48 g, quantitative) as a pale-yellow powder.

後処理

  1. customobtained above, and the mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate (100 mL)
  4. washThe mixture was washed with water (50 mL) and saturated brine (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50→0/100), and fractions
  9. additioncontaining the desired product
  10. concentrationwere concentrated under reduced pressure

出典と根拠

ORDレコード
ord-37e902198c2f41b8a7e58f4f5d5f4863
出典データセット
uspto-grants-2012_11
特許番号
US08304557B2

反応ノート

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