Water → 1-[4-[4-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-6-(4-methanesulfonyl-phenoxy)-pyrimidin-5-yl]-ethanone

HRID 2067133노트

반응식

HRID 2067133 반응식
Cl[C:2]1[C:7]([C:8](=[O:10])[CH3:9])=[C:6]([O:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[N:5]=[CH:4][N:3]=1.[CH:22]([C:25]1[N:29]=[C:28]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[O:27][N:26]=1)([CH3:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:22]([C:25]1[N:29]=[C:28]([CH:30]2[CH2:35][CH2:34][N:33]([C:2]3[C:7]([C:8](=[O:10])[CH3:9])=[C:6]([O:11][C:12]4[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=4)[N:5]=[CH:4][N:3]=3)[CH2:32][CH2:31]2)[O:27][N:26]=1)([CH3:24])[CH3:23]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 242088454-(3-(Propan-2-yl)-1,2,4-oxadiazol-5-yl)piperidineHCID 859844451-[4-Chloro-6-(4-methanesulfonyl-phenoxy)-pyrimidin-5-yl]-ethanone

생성물 1

HCID 582164601-[4-[4-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-6-(4-methanesulfonyl-phenoxy)-pyrimidin-5-yl]-ethanone수율 20%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1-[4-chloro-6-(4-methanesulfonyl-phenoxy)-pyrimidin-5-yl]-ethanone (0.21 mmol, 70 mg) and 4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidine (0.21 mmol, 49 mg) in N,N-dimethyl formamide (500 uL) was added potassium carbonate (0.21 mmol, 29 mg). The mixture was microwaved at 100° C. for 150 seconds. Its progress was monitored by thin layer chromatography and LCMS. The reaction was treated with water and the desired compound was extracted in ethyl acetate. Organic layer was evaporated in vacuo. Purification by HPLC provided Compound A165 as a white solid (20 mg, 20%). 1H-NMR (400 MHz, CDCl3) δ(ppm): 8.24 (s, 1H); 8.01 (d, 2H); 7.32 (d, 2H); 4.02 (m, 2H); 3.22 (m, 3H); 3.10 (m, 1H); 3.08 (s, 3H); 2.69 (s, 3H), 2.18 (m, 2H), 2.02 (m, 2H); 1.35 (d, 6H). LCMS (ESI), m/z 486.3 (M+H+, 100%).

후처리

  1. customThe mixture was microwaved at 100° C. for 150 seconds
  2. extractionthe desired compound was extracted in ethyl acetate
  3. customOrganic layer was evaporated in vacuo
  4. customPurification by HPLC

출처 및 근거

ORD 기록
ord-422d6efb945e4a898727c0ca7c6479c1
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293751B2

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