N-[4-(2,4,6-Trimethylphenyl)-2-thiazolyl]-1-tert-butoxycarbonyl-indoline-2-carboxamide → N-[4-(2,4,6-Trimethylphenyl)-2-thiazolyl]indoline-2-carboxamide

HRID 1531592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1531592
[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>ClCCl.FC(F)(F)C(O)=O.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

Komponenten

5

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

35 g of N-[4-(2,4,6-trimethylphenyl)-2-thiazolyl]-1-tert-butoxycarbonyl-indoline-2-carboxamide are dissolved in 200 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 6.0(s,1H); 6.9-7.6(m,7H); 12.1(s,1H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-6bf2f17ddda5444dbf8a2d29d626846a
Quelldatensatz
uspto-grants-2001_03
Patentnummer
USRE037094E1

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