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Water → 3-Methyl-pyridine-2-carboxylic acid [1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropylmethyl]-amide

HRID 578859
ノート
印刷プレビュー

反応式

HRID 578859 の反応式
[Cl:1][C:2]1[C:3]([C:12]2([CH2:15][NH2:16])[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.[CH3:24][C:25]1[C:26]([C:31](Cl)=[O:32])=[N:27][CH:28]=[CH:29][CH:30]=1.O>ClCCl>[Cl:1][C:2]1[C:3]([C:12]2([CH2:15][NH:16][C:31]([C:26]3[C:25]([CH3:24])=[CH:30][CH:29]=[CH:28][N:27]=3)=[O:32])[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 204875083-Methylpyridine-2-carbonyl chlorideHCID 71559141(1-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)cyclopropyl)methanamine

生成物 1

HCID 715588383-Methyl-pyridine-2-carboxylic acid [1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropylmethyl]-amide収率 39.2%

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

180 mg of C-[1-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-methylamine (step 1) was dissolved in 5 ml of dichloromethane and cooled to 0° C. Then 145 mg of triethylamine was added, followed by dropwise addition of a solution of 112 mg of 3-methyl-pyridine-2-carbonyl chloride in 1 ml of dichloromethane. The reaction mixture was stirred at ambient temperature for 2 hours. Then 6 ml of water were added, the resulting phases were separated and the organic phase was washed with aqueous 2N sodium hydroxide solution, then with 1N aqueous hydrochloric acid and brine, dried over sodium sulfate, filtered and concentrated. Thus, 282 mg of crude material was obtained as a brown sticky solid. This residue was purified by chromatography on silica gel, with cyclohexane/ethyl acetate (1:1) as a eluent. Thus, 104 mg of 3-methyl-pyridine-2-carboxylic acid [1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropylmethyl]-amide was obtained as a sticky oil. 1H-NMR (CDCl3): 8.64 ppm (s, 1H), 8.35 ppm (m, 2H), 7.90 ppm (s, 1H), 7.53 ppm (m, 1H), 7.27 ppm (m, 1H), 3.74 (d, 2H), 2.60 ppm (s, 3H), 1.16 ppm (m, 2H), 1.12 ppm (m, 2H).

後処理

  1. customthe resulting phases were separated
  2. washthe organic phase was washed with aqueous 2N sodium hydroxide solution
  3. dry with materialwith 1N aqueous hydrochloric acid and brine, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThus, 282 mg of crude material was obtained as a brown sticky solid
  7. customThis residue was purified by chromatography on silica gel, with cyclohexane/ethyl acetate (1:1) as a eluent

出典と根拠

ORDレコード
ord-764959b17c004fffbffc7c29b64d1048
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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