Triethylamine → N-(4-bromo-3-methyl-5-isoxazolyl)-2-[N-(3-carboxyphenyl)aminocarbonyl]thiophene-3-sulfonamide

HRID 1067620

반응식

HRID 1067620 반응식
CCN(CC)CC.[NH2:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12]([O:14]CC)=[O:13].N1P(Cl)(Cl)=NP(Cl)(Cl)=NP=1(Cl)Cl.[Br:32][C:33]1[C:34]([CH3:51])=[N:35][O:36][C:37]=1[NH:38][S:39]([C:42]1[CH:46]=[CH:45][S:44][C:43]=1[C:47](OC)=[O:48])(=[O:41])=[O:40]>C1COCC1.O>[Br:32][C:33]1[C:34]([CH3:51])=[N:35][O:36][C:37]=1[NH:38][S:39]([C:42]1[CH:46]=[CH:45][S:44][C:43]=1[C:47]([NH:8][C:9]1[CH:19]=[CH:18][CH:17]=[C:11]([C:12]([OH:14])=[O:13])[CH:10]=1)=[O:48])(=[O:40])=[O:41]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 220225HexachlorocyclotriphosphazeneHCID 10833686N-(4-Bromo-3-methyl-5-isoxazolyl)-2-(carbomethoxy)thiophene-3-sulfonamide

생성물 1

HCID 10576889N-(4-bromo-3-methyl-5-isoxazolyl)-2-[N-(3-carboxyphenyl)aminocarbonyl]thiophene-3-sulfonamide수율 13.9%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Et3N (2.27 mL, 16. mmol), ethyl 3-aminobenzoate (836 mL, 5.44 mmol) and phosphonitrilic chloride trimer (1.89 g, 5.44 mmol) were sequentially added to a solution of N-(4-bromo-3-methyl-5-isoxazolyl)-2-(carbonyl)thiophene-3-sulfonamide (Example 12) (1 g, 2.27 mmol) in dry THF (20 mL). The reaction was stirred at room temperature for 1 hour and cooled. Water (5 mL) was added to quench the reaction. The resulting solution was concentrated on a rotavap. The residue was diluted with EtOAc and washed with 2N HCl (2×150 mL). The organic layer was dried (MgSO4). The solid was filtered off and the filtrate was concentrated. The residue was treated with 1N NaOH (200 mL) and stirred at 0° C. for 15 minutes. The mixture was then acidified with conc. HCl to pH˜1. The resulting yellow precipitate was filtered off and recrystallized from CH3CN/H2O to give N-(4-bromo-3-methyl-5-isoxazolyl)-2-[N-(3-carboxyphenyl)aminocarbonyl]thiophene-3-sulfonamide (153 mg., 11.6%) as a yellowish powder, m.p. 183-185° C.

후처리

  1. temperaturecooled
  2. customto quench
  3. customthe reaction
  4. concentrationThe resulting solution was concentrated on a rotavap
  5. additionThe residue was diluted with EtOAc
  6. washwashed with 2N HCl (2×150 mL)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationThe solid was filtered off
  9. concentrationthe filtrate was concentrated
  10. additionThe residue was treated with 1N NaOH (200 mL)
  11. stirringstirred at 0° C. for 15 minutes
  12. filtrationThe resulting yellow precipitate was filtered off
  13. customrecrystallized from CH3CN/H2O

출처 및 근거

ORD 기록
ord-2040520efd2c43baa3aa24c7ad4c1d78
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248767B1

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