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

HRID 990047

反応式

HRID 990047 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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 2 N 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 1 N 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.

後処理

  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 2 N 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 1 N NaOH (200 mL)
  11. stirringstirred at 0° C. for 15 minutes
  12. filtrationThe resulting yellow precipitate was filtered off
  13. customrecrystallized from CH3CN/H2O

出典と根拠

ORDレコード
ord-8714356765f54754b2efa4fa960110eb
出典データセット
uspto-grants-2002_10
特許番号
US06458805B2

関連ノート

読み込み中…