Trifluoroacetic acid → N-[4-(2,4,6-Trimethylphenyl)-2-thiazolyl]indoline-2-carboxamide

HRID 2082408ノート

反応式

HRID 2082408 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[C:10]1[N:11]=[C:12]([NH:15][C:16]([CH:18]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]2C(OC(C)(C)C)=O)=[O:17])[S:13][CH:14]=1.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[C:10]1[N:11]=[C:12]([NH:15][C:16]([CH:18]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19]2)=[O:17])[S:13][CH:14]=1

参加物

5

反応物 2

HCID 6422Trifluoroacetic acidHCID 21249482N-[4-(2,4,6-Trimethylphenyl)-2-thiazolyl]-1-tert-butoxycarbonyl-indoline-2-carboxamide

生成物 1

HCID 21249485N-[4-(2,4,6-Trimethylphenyl)-2-thiazolyl]indoline-2-carboxamide収率 88%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

35 g of N-[4-(2,4,6-trimethylphenyl)-2-thiazolyl]-1-tert-butoxycarbonyl-indoline-2-carboxamide are dissolved in 200 ml of dry dichloromethane and 40 ml of trifluoroacetic acid are added dropwise. The reaction mixture is kept at ambient temperature for 2 hours and then evaporated to dryness. The residue obtained is taken up in 150 ml of ethyl acetate. The organic solution is washed with 1N aqueous sodium hydroxide solution and then with water saturated with NaCl and dried over anhydrous magnesium sulphate. After removal of the ethyl acetate, the final product is obtained, from which the salt is prepared by the action of gaseous HCl in isopropanol. The hydrochloride melts at 212° C. Yield 88%. Salt: 1H NMR: 80 MHz(DMSOd6) δ(ppm): 2.1(s,6H); 2.4(s,3H); 3.2-3.8(m,2H); 5.0(m,1H); 6.0(s,1H; 6.9-7.6(m,7H); 12.1(s,1H).

後処理

  1. customevaporated to dryness
  2. customThe residue obtained
  3. washThe organic solution is washed with 1N aqueous sodium hydroxide solution
  4. dry with materialwith water saturated with NaCl and dried over anhydrous magnesium sulphate
  5. customAfter removal of the ethyl acetate

出典と根拠

ORDレコード
ord-56b28b0be4944494aee74a2b0ed9286d
出典データセット
uspto-grants-1993_02
特許番号
US05189049

反応ノート

読み込み中…