Carbon Dioxide → Upb5G360MA

HRID 1951022노트

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HRID 1951022 반응식
[CH3:1][NH2:2].Cl.CN.[OH-].[Na+].C(=O)=O.[O:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.[N:18]1[O:19][N:20]=[C:21]2[CH:26]=[C:25]([C:27](Cl)=[O:28])[CH:24]=[CH:23][C:22]=12>CO.C(Cl)(Cl)Cl.[Pd].C(N(CC)CC)C>[CH3:1][N:2]([CH:14]1[CH2:15][CH2:16][O:11][CH2:12][CH2:13]1)[C:27]([C:25]1[CH:24]=[CH:23][C:22]2=[N:18][O:19][N:20]=[C:21]2[CH:26]=1)=[O:28]

참가 물질

11

반응물 6

HCID 280Carbon DioxideHCID 6329MethylamineHCID 14798Sodium HydroxideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 27354532,1,3-Benzoxadiazole-5-carbonyl chlorideHCID 6364545Methylamine hydrochloride

생성물 1

HCID 25104045Upb5G360MA

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 887Methanol용매HCID 6212Chloroform용매HCID 8471Triethylamine용매

실험 절차

Methylamine, generated by heating a mixture of methylamine hydrochloride (10 g) and sodium hydroxide pellets (18 g), was condensed (dry ice trap) into a solution of tetrahydro-4H-pyran-4-one (1.0 g, 10 mmol) in methanol (50 ml). 10% Pd on C (350 mg) was added and the mixture was hydrogenated at room temperature for 7 hours. The solids were filtered off and the filtrate concentrated under vacuum. The residue was dissolved in chloroform (70 ml) and triethylamine (2 ml) and a solution of [2,1,3]-benzoxadiazole-5-carbonylchloride (500 mg, 2.73 mmol) in chloroform (10 ml) was added slowly. After stirring the reaction mixture for 30 minutes, the organic phase was extracted with 100 ml of water and sulfuric acid (→pH 2) and the aqueous phase re-extracted with chloroform (100 ml), dried over magnesium sulfate, and concentrated under vacuum to give an oil. The crude product was purified by silica gel chromatography eluting ethyl acetate/hexane (75:25) and chloroform/acetone (85:15) to give the title product as a white solid after crystallization from ethyl acetate. Mp=160-2° C., LC-MS, MH+=262; 1H NMR (300 MHz, CDCl3, 2 rotamers) δ 7.93 (d, 1H, J=9.0 Hz); 7.84 (s, 1H); 7.42 (d, 1H, J=9.0 Hz); 4.90-4.70 and 4.20-3.10 (m+m, 5H); 2.927 (s, 3H); 2.1-1.5 ppm (m, 4H).

후처리

  1. temperatureby heating
  2. filtrationThe solids were filtered off
  3. concentrationthe filtrate concentrated under vacuum
  4. dissolutionThe residue was dissolved in chloroform (70 ml)
  5. extractionthe organic phase was extracted with 100 ml of water and sulfuric acid (→pH 2)
  6. extractionthe aqueous phase re-extracted with chloroform (100 ml)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. customto give an oil
  10. customThe crude product was purified by silica gel chromatography
  11. washeluting ethyl acetate/hexane (75:25) and chloroform/acetone (85:15)

출처 및 근거

ORD 기록
ord-fa2f450e9cb74c6e9a524663bddbe8a0
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404682B2

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