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Water → N-{1-[1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-ethyl}-2,6-difluoro-benzamide

HRID 578857
ノート
印刷プレビュー

反応式

HRID 578857 の反応式
[Cl:1][C:2]1[C:3]([C:12]2([CH:15]([NH2:17])[CH3:16])[CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(N(CC)CC)C.[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:27]=1[C:28](Cl)=[O:29].O>ClCCl>[Cl:1][C:2]1[C:3]([C:12]2([CH:15]([NH:17][C:28](=[O:29])[C:27]3[C:26]([F:25])=[CH:34][CH:33]=[CH:32][C:31]=3[F:35])[CH3:16])[CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 715591401-[1-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-ethylamine

生成物 1

HCID 71558840N-{1-[1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-ethyl}-2,6-difluoro-benzamide収率 97.4%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

反応条件

温度
0 °C

実験手順

100 mg of 1-[1-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-ethylamine (step 4) was dissolved in 4 ml of dichloromethane and cooled to 0° C. Then 76 mg of triethylamine was added, followed by dropwise addition of a solution of 67 mg of 2,6-difluorobenzoyl chloride in 1 ml of dichloromethane. The reaction mixture was stirred at ambient temperature for 2 hours. Then 20 ml of water were added and the mixture was extracted with 20 ml dichloromethane. The organic phase was dried over sodium sulfate, filtered and concentrated. Thus, 162 mg of crude material was obtained as a pale yellow oil. This residue was purified by chromatography on silica gel, with cyclohexane/ethyl acetate (85:15) as a eluent. Thus, 149 mg of N-{1-[1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-ethyl}-2,6-difluoro-benzamide was obtained as a colourless sticky oil. 1H-NMR (CDCl3): 8.67 ppm (s, 1H), 7.93 ppm (s, 1H), 7.33 ppm (m, 1H), 6.93 ppm (t, 2H), 6.69 ppm (d, 1H, broad), 4.37 ppm (m, 1H), 1.25 ppm (d, 3H), 1.20 ppm (m, 4H).

後処理

  1. extractionthe mixture was extracted with 20 ml dichloromethane
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThus, 162 mg of crude material was obtained as a pale yellow oil
  6. customThis residue was purified by chromatography on silica gel, with cyclohexane/ethyl acetate (85:15) as a eluent

出典と根拠

ORDレコード
ord-138fddc5425e4cd29f59e2a8766235a5
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09040708B2

反応ノート

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