Water → 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [4-chloro-2-methyl-6-(thietan-3-ylcarbamoyl)-phenyl]-amide

HRID 2060942ノート

反応式

HRID 2060942 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:29])[C:5]2[N:10]=[C:9]([C:11]3[N:15]([C:16]4[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=4)[N:14]=[C:13]([C:23]([F:26])([F:25])[F:24])[CH:12]=3)[O:8][C:7](=[O:27])[C:6]=2[CH:28]=1.C(N(CC)CC)C.Br.[S:38]1[CH2:41][CH:40]([NH2:42])[CH2:39]1.O>O1CCCC1>[Cl:1][C:2]1[CH:28]=[C:6]([C:7](=[O:27])[NH:42][CH:40]2[CH2:41][S:38][CH2:39]2)[C:5]([NH:10][C:9]([C:11]2[N:15]([C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=3)[N:14]=[C:13]([C:23]([F:24])([F:25])[F:26])[CH:12]=2)=[O:8])=[C:4]([CH3:29])[CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 231503516-chloro-2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-8-methylbenzo[d][1,3]oxazin-4-oneHCID 53346555Thietan-3-amine hydrobromide2 回

生成物 1

HCID 593935962-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [4-chloro-2-methyl-6-(thietan-3-ylcarbamoyl)-phenyl]-amide収率 41%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 6-chloro-2-[1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazin-4-one (500 mg, 1.13 mmol) [prepared according to WO 02/48115, example 2D] in tetrahydrofuran (10 ml) is added triethylamine (0.4 ml, 2.87 mmol) and 3-thietanamine hydrobromide salt [the product of step 2] (250 mg, 1.47 mmol), and the mixture is heated to reflux overnight. The cooled reaction mixture is poured into water, extracted with ethyl acetate, the combined organic layers washed with water and brine, dried (Na2SO4), filtered, and concentrated. The crude product is purified by flash chromatography (ethyl acetate/hexane 1:2) to afford 250 mg (41%) of the title compound as a white solid.

後処理

  1. temperaturethe mixture is heated
  2. temperatureto reflux overnight
  3. customThe cooled reaction mixture
  4. extractionextracted with ethyl acetate
  5. washthe combined organic layers washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified by flash chromatography (ethyl acetate/hexane 1:2)

出典と根拠

ORDレコード
ord-f8559c62c3a14b92930099d1e82a8f8d
出典データセット
uspto-grants-2012_10
特許番号
US08278464B2

反応ノート

読み込み中…