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

HRID 1424540
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HRID 1424540 반응식
[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
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참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매

3
HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
100 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-f0eb1f100e33481dbc991eb271efab0d
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08927726B2

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