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Triethylamine → 2-[2-(4-Trifluoromethyl-phenyl)-vinyl]-oxazole-4-carboxylic acid [4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-amide

HRID 1271437
ノート
印刷プレビュー

反応式

HRID 1271437 の反応式
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[O:12][CH:13]=[C:14]([C:16]([OH:18])=O)[N:15]=2)=[CH:5][CH:4]=1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[N:39]1([CH2:44][CH2:45][CH2:46][CH2:47][C:48]2[CH:53]=[CH:52][C:51]([NH2:54])=[CH:50][CH:49]=2)[CH:43]=[CH:42][N:41]=[N:40]1>ClCCl.C(OCC)(=O)C>[N:39]1([CH2:44][CH2:45][CH2:46][CH2:47][C:48]2[CH:49]=[CH:50][C:51]([NH:54][C:16]([C:14]3[N:15]=[C:11]([CH:10]=[CH:9][C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:20])[F:19])=[CH:8][CH:7]=4)[O:12][CH:13]=3)=[O:18])=[CH:52][CH:53]=2)[CH:43]=[CH:42][N:41]=[N:40]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 184535324-(4-[1,2,3]Triazol-1-yl-butyl)-phenylamineHCID 694874342-{2-[4-(Trifluoromethyl)phenyl]ethenyl}-1,3-oxazole-4-carboxylic acid

生成物 1

HCID 727876562-[2-(4-Trifluoromethyl-phenyl)-vinyl]-oxazole-4-carboxylic acid [4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-amide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-[2-(4-Trifluoromethyl-phenyl)-vinyl]-oxazole-4-carboxylic acid (100 mg, 0.35 mmol), N-ethyl-N′-(3-dimethyl-aminopropyl)carbodiimide hydrochloride (101 mg, 0.53 mmol), 1-Hydroxybenzotriazole hydrate (73 mg, 0.53 mmol) and triethylamine (71 mg, 0.71 mmol) are suspended in dichloromethane (5 ml). After stirring at room temperature for 15 min 4-(4-[1,2,3]Triazol-1-yl-butyl)-phenylamine (84 mg, 0.39 mmol) is added and stirring is continued for 20 h. Ethyl acetate (10 ml) is added and the mixture washed with aq. HCl (1N, 10 ml), sat. NaHCO3, (10 ml), dried over sodium sulfate and concentrated in vacuo. The crude product is purified by flash column chromatography (ethyl acetate/heptane 9:1) yielding 2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazole-4-carboxylic acid [4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-amide 11 as a colorless solid. Yield 109 mg (64%); m.p. 183–185° C.

後処理

  1. additionis added
  2. washthe mixture washed with aq. HCl (1N, 10 ml), sat. NaHCO3, (10 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by flash column chromatography (ethyl acetate/heptane 9:1)

出典と根拠

ORDレコード
ord-cceee2bdfecf4a319ff162115d84d0bc
出典データセット
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07205326B2

反応ノート

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