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Propionyl chloride → N-(1-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-ethyl)-propionamide

HRID 2045954
ノート
印刷プレビュー

反応式

HRID 2045954 の反応式
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].CCN(C(C)C)C(C)C.[Cl:15][C:16]1[CH:17]=[C:18]([C:23]2([C:37]([F:40])([F:39])[F:38])[O:27][N:26]=[C:25]([C:28]3[S:32][C:31]([CH:33]([NH2:35])[CH3:34])=[C:30]([CH3:36])[CH:29]=3)[CH2:24]2)[CH:19]=[C:20]([Cl:22])[CH:21]=1>ClCCl>[Cl:15][C:16]1[CH:17]=[C:18]([C:23]2([C:37]([F:39])([F:38])[F:40])[O:27][N:26]=[C:25]([C:28]3[S:32][C:31]([CH:33]([NH:35][C:1](=[O:4])[CH2:2][CH3:3])[CH3:34])=[C:30]([CH3:36])[CH:29]=3)[CH2:24]2)[CH:19]=[C:20]([Cl:22])[CH:21]=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 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 665872941-{5-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-ethylamine

生成物 1

HCID 54766913N-(1-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-ethyl)-propionamide収率 30.9%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

Propionyl chloride (20 mg) and Hünig base (70 μl) are added to a solution of 1-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-ethylamine (60 mg) in dichloromethane (1 ml). After 19 hours at room temperature, the reaction is quenched with water. The reaction mixture is extracted three times with dichloromethane. The combined organic phases are dried over MgSO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield N-(1-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-ethyl)-propionamide (21 mg, compound 1.49 in Table 1) as a light yellow oil. MS (HPLC/MS): 479 (MH+). Retention time: 2.01 min.

後処理

  1. customthe reaction is quenched with water
  2. extractionThe reaction mixture is extracted three times with dichloromethane
  3. dry with materialThe combined organic phases are dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified on a semi-preparative HPLC

出典と根拠

ORDレコード
ord-74bb86adb45049019768c0ba16cf96f9
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08592418B2

反応ノート

読み込み中…

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