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Potassium Iodide → N-Cyclopropyl-4-oxazol-5-yl-N-[1-(1-trifluoromethyl-cyclopropylmethyl)-piperidin-4-yl]-benzamide

HRID 1424540
ノート
印刷プレビュー

反応式

HRID 1424540 の反応式
[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][C:25](O)([CH3:27])[CH3:26])[CH2:20][CH2:19]2)[C:5](=[O:17])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:16][CH:15]=[N:14][CH:13]=3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[F:29][C:30]([F:41])([F:40])C1(COS(C)(=O)=O)CC1.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>CN1CCCC1=O.O.C(OCC)(=O)C>[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][C:25]3([C:30]([F:41])([F:40])[F:29])[CH2:27][CH2:26]3)[CH2:20][CH2:19]2)[C:5](=[O:17])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:16][CH:15]=[N:14][CH:13]=3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]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

8

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 86649942(1-(Trifluoromethyl)cyclopropyl)methyl methanesulfonateHCID 86709612N-Cyclopropyl-N-[1-(2-hydroxy-2-methyl-propyl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide

生成物 1

HCID 73053286N-Cyclopropyl-4-oxazol-5-yl-N-[1-(1-trifluoromethyl-cyclopropylmethyl)-piperidin-4-yl]-benzamide

試薬・触媒・溶媒

3
HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
100 °C

実験手順

A mixture of N-cyclopropyl-N-[1-(2-hydroxy-2-methyl-propyl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide (80 mg), methanesulfonic acid (1-trifluoromethyl-cyclopropyl)methyl ester (269 mg), K2CO3 (81 mg), and potassium iodide (38 mg) in N-methyl-2-pyrrolidone (3 mL) is stirred at 100° C. for two days. After cooling to room temperature, ethyl acetate and water are added to the mixture. The organic phase is separated, dried over MgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel [dichloromethane/7 M ammonia in methanol 9:1→7:3] and the crude product is purified by preparative HPLC to give the title compound. LC (method 3): tR=1.22 min; Mass spectrum (ESI+): m/z=434 [M+H]+.

後処理

  1. temperatureAfter cooling to room temperature
  2. customThe organic phase is separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on silica gel [dichloromethane/7 M ammonia in methanol 9:1→7:3]
  6. customthe crude product is purified by preparative HPLC

出典と根拠

ORDレコード
ord-f0eb1f100e33481dbc991eb271efab0d
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08927726B2

反応ノート

読み込み中…

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