Triethylamine → N-[4-(4-Trifluoromethyl-2,6-dimethoxyphenyl)-2-thiazolyl]-1-(tert-butoxycarbonylmethyl)indole-2-carboxamide

HRID 2257132

Reaktionsgleichung

Reaktionsgleichung von HRID 2257132
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[C:12]([O:13][CH3:14])=[CH:11][C:10]([C:15]([F:18])([F:17])[F:16])=[CH:9][C:8]=2[O:19][CH3:20])[N:6]=1.[C:21]([O:25][C:26]([CH2:28][N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[C:30]1[C:38](O)=[O:39])=[O:27])([CH3:24])([CH3:23])[CH3:22].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl.O>[F:18][C:15]([F:16])([F:17])[C:10]1[CH:11]=[C:12]([O:13][CH3:14])[C:7]([C:5]2[N:6]=[C:2]([NH:1][C:38]([C:30]3[N:29]([CH2:28][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[C:37]4[C:32]([CH:31]=3)=[CH:33][CH:34]=[CH:35][CH:36]=4)=[O:39])[S:3][CH:4]=2)=[C:8]([O:19][CH3:20])[CH:9]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 190280212-Amino-4-(4-trifluoromethyl-2,6-dimethoxyphenyl)thiazoleHCID 21749024N-(tert-butoxycarbonylmethyl)-2-indolecarboxylic acid

Produkt 1

HCID 19028034N-[4-(4-Trifluoromethyl-2,6-dimethoxyphenyl)-2-thiazolyl]-1-(tert-butoxycarbonylmethyl)indole-2-carboxamideAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 0.609 g of 2-amino-4-(4-trifluoromethyl-2,6-dimethoxyphenyl)thiazole, 0.606 g of N-(tert-butoxycarbonylmethyl)-2-indolecarboxylic acid, 1.062 g of BOP and 0.243 g of triethylamine in 30 ml of DCM is stirred at r.t. for 24 hours. 50 ml of water are then added, and the organic phase is separated after settling has taken place, dried over sodium sulphate and evaporated under vacuum. The residue is chromatographed on silica H, eluting with a DCM/AcOEt (100:5; v/v) mixture. 0.79 g of the expected product is obtained after crystallization in ether, m.p.=214°-216° C.

Aufarbeitung

  1. customthe organic phase is separated after settling
  2. dry with materialdried over sodium sulphate
  3. customevaporated under vacuum
  4. customThe residue is chromatographed on silica H
  5. washeluting with a DCM/AcOEt (100:5; v/v) mixture

Quellen und Nachweise

ORD-Eintrag
ord-45d196adc7644d52b2b1ebfe1993d1f2
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05656648

Verknüpfte Notizen

Wird geladen…