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Potassium Carbonate → (3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-(2-thiophen-2-yl-propyl)-amino]-propoxy}-phenyl)-acetic Acid Methyl Ester

HRID 902683
ノート
印刷プレビュー

反応式

HRID 902683 の反応式
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14]Br)[CH:6]=1.[Cl:17][C:18]1[C:33]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:31]=[CH:30][C:19]=1[CH2:20][NH:21][CH2:22][CH:23]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)[CH3:24].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:21]([CH2:20][C:19]2[CH:30]=[CH:31][CH:32]=[C:33]([C:34]([F:37])([F:35])[F:36])[C:18]=2[Cl:17])[CH2:22][CH:23]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)[CH3:24])[CH:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 10565189Methyl [3-(3-bromopropoxy)phenyl]acetateHCID 69253724(2-Chloro-3-trifluoromethyl-benzyl)-(2-thiophen-2-yl-propyl)-amine

生成物 1

HCID 69253058(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-(2-thiophen-2-yl-propyl)-amino]-propoxy}-phenyl)-acetic Acid Methyl Ester収率 33.1%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

A solution of (3-{3-bromo-propoxy}-phenyl)acetic acid methyl ester (41 mg, 0.14 mmol) and (2-chloro-3-trifluoromethyl-benzyl)-(2-thiophen-2-yl-propyl)-amine (50 mg, 10.14 mmol) in acetonitrile (10 ml) was treated with solid potassium carbonate (24.9 mg, 0.18 mmol). The reaction was heated to reflux and stirred for 48 h. Upon cooling to room temperature, the reaction was filtered through a pad of celite, washed with EtOAc, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatograph (EtOAc:Hexane/20:80) to give the title compound as an oil (25 mg, 30%). MS m/e 540.6 (M+H)+.

後処理

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. filtrationthe reaction was filtered through a pad of celite
  4. washwashed with EtOAc
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe crude product was purified by column chromatograph (EtOAc:Hexane/20:80)

出典と根拠

ORDレコード
ord-12a063255283496ca8e37e3ee73fe9c2
出典データセット
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07365085B2

反応ノート

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