Potassium Carbonate → HCID 59481195, 화합물

HRID 560866노트

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HRID 560866 반응식
CS([O:5][CH2:6][CH2:7][N:8]1[C:12](=[O:13])[N:11]([C:14]2[S:15][C:16]([C:20](=[O:29])[NH:21][CH2:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[C:17]([CH3:19])[N:18]=2)[CH:10]=[N:9]1)(=O)=O.[C:30](=[O:33])([O-])[O-].[K+].[K+].[F:36][C:37]1[CH:42]=[CH:41][C:40]([CH2:43][NH2:44])=[CH:39][CH:38]=1>O1CCCC1>[F:36][C:37]1[CH:42]=[CH:41][C:40]([CH2:43][NH:44][C:30](=[O:33])[O:5][CH2:6][CH2:7][N:8]2[C:12](=[O:13])[N:11]([C:14]3[S:15][C:16]([C:20](=[O:29])[NH:21][CH2:22][C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)=[C:17]([CH3:19])[N:18]=3)[CH:10]=[N:9]2)=[CH:39][CH:38]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 673264-FluorobenzylamineHCID 594812642-(4-(4-methyl-5-(pyridin-3-ylmethylcarbamoyl)thiazol-2-yl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)ethyl methanesulfonate

생성물 1

HCID 59481195HCID 59481195, 화합물수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To the solution of 2-(4-(4-methyl-5-(pyridin-3-ylmethylcarbamoyl)thiazol-2-yl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)ethyl methanesulfonate (0.40 g, 0.91 mmol) in anhydrous tetrahydrofuran (10 mL) was added potassium carbonate (0.32 g, 2.28 mmol). The reaction mixture was stirred at ambient temperature for 1 minute, followed by the addition of (4-fluorophenyl)methanamine (0.10 mL, 0.91 mmol). The reaction mixture was stirred at ambient temperature for 17 hours, and then partitioned between ethyl acetate and brine. The organic layer was separated, washed with brine, dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with ethyl acetate to afford the title compound as a white solid in 77% yield (0.36 g): mp 149-150° C. (ethyl acetate): 1H NMR (300 MHz, CDCl3) δ 8.58 (br s, 1H), 8.49 (br s, 1H), 8.22 (s, 1H), 7.72-7.64 (m, 1H), 7.31-7.14 (m, 3H), 7.00-6.89 (m, 2H), 6.54 (t, J=5.8 Hz, 1H), 5.33 (t, J=5.9 Hz, 1H), 4.59 (d, J=5.8 Hz, 2H), 4.38 (t, J=5.1 Hz, 2H), 4.25 (d, J=5.9 Hz, 2H), 4.06 (t, J=5.1 Hz, 2H), 2.62 (s, 3H): MS (ES+) m/z 512.4 (M+1).

후처리

  1. stirringThe reaction mixture was stirred at ambient temperature for 17 hours
  2. custompartitioned between ethyl acetate and brine
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography
  9. washeluted with ethyl acetate

출처 및 근거

ORD 기록
ord-fbd3f85715f14bcd8b745293d3dbc707
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063084B2

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