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Potassium Carbonate → 5-Ethyl-2-{4-[3-(2-fluoro-4-methanesulfonyl-phenoxymethyl)-[1,2,4]triazol-1-yl]-piperidin-1-yl}-pyrimidine

HRID 1928597
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인쇄 미리보기

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HRID 1928597 반응식
Cl.[F:2][C:3]1[CH:21]=[C:20]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:19]=[CH:18][C:4]=1[O:5][CH2:6][C:7]1[N:11]=[CH:10][N:9]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[N:8]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:33]1[N:38]=[CH:37][C:36]([CH2:39][CH3:40])=[CH:35][N:34]=1>CN(C)C=O>[CH2:39]([C:36]1[CH:35]=[N:34][C:33]([N:15]2[CH2:16][CH2:17][CH:12]([N:9]3[CH:10]=[N:11][C:7]([CH2:6][O:5][C:4]4[CH:18]=[CH:19][C:20]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:21][C:3]=4[F:2])=[N:8]3)[CH2:13][CH2:14]2)=[N:38][CH:37]=1)[CH3:40]
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 35727632-Chloro-5-ethylpyrimidineHCID 687280424-[3-(2-Fluoro-4-methanesulfonyl-phenoxymethyl)-[1,2,4]triazol-1-yl]-piperidine hydrochloride2회

생성물 1

HCID 251760355-Ethyl-2-{4-[3-(2-fluoro-4-methanesulfonyl-phenoxymethyl)-[1,2,4]triazol-1-yl]-piperidin-1-yl}-pyrimidine

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
90 °C

실험 절차

A mixture of 4-[3-(2-fluoro-4-methanesulfonyl-phenoxymethyl)-[1,2,4]triazol-1-yl]-piperidine hydrochloride salt (Intermediate 6, 0.100 g, 0.256 mmol), potassium carbonate (0.106 g, 0.768 mmol) and 2-chloro-5-ethyl-pyrimidine (0.062 mL, 0.512 mmol) in dimethylformamide (2 mL) was heated at 90° C. for 4 hours or until the starting material was consumed. The reaction was cooled to room temperature, the solution was diluted with water and extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over sodium sulfate, filtered and concentration in vacuo. The residue was chromatographed on silica gel (1:1 Hex/EtOAc) to afford the desired product. 1H NMR (CDCl3): δ 8.22 (2H, s), 8.17 (1H, s), 7.68 (2H, m), 7.38 (1H, m), 5.28 (2H, s), 4.92 (2H, d), 4.47 (1H, m), 3.08 (3H, s), 2.94 (2H, m), 2.48 (2H, q), 2.27 (1H, m), 2.18 (1H, m), 1.98 (2H, m), 1.20 (3H, t).

후처리

  1. customwas consumed
  2. temperatureThe reaction was cooled to room temperature
  3. additionthe solution was diluted with water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentration in vacuo
  10. customThe residue was chromatographed on silica gel (1:1 Hex/EtOAc)

출처 및 근거

ORD 기록
ord-d62d34a3943f448791076a23e5876b69
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08183381B2

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