Ethyl Acetate → HCID 73775810, Verbindung

HRID 588069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588069
[CH3:1][NH:2][C:3]1[S:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.[N:12]([C:15]1[N:20]=[C:19]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[CH:18]=[C:17]([O:27][CH2:28][C:29]([F:32])([F:31])[F:30])[N:16]=1)=[C:13]=[O:14].CCOC(C)=O>C(Cl)Cl>[F:26][C:23]([F:24])([F:25])[CH2:22][O:21][C:19]1[CH:18]=[C:17]([O:27][CH2:28][C:29]([F:32])([F:31])[F:30])[N:16]=[C:15]([NH:12][C:13](=[O:14])[N:2]([CH3:1])[C:3]2[S:4][C:5]([C:8]([F:10])([F:9])[F:11])=[CH:6][CH:7]=2)[N:20]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 576517972-Isocyanato-4,6-bis(2,2,2-trifluoroethoxy)pyrimidineHCID 86718388N-Methyl-5-(trifluoromethyl)thiophen-2-amine

Produkt 1

HCID 73775810HCID 73775810, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-methyl-5-(trifluoromethyl)thiophen-2-amine in CH2Cl2 (2 mL) was added 2-isocyanato-4,6-bis(2,2,2-trifluoroethoxy)pyrimidine (1.6 mL, 1.0 M in THF) (prepared as described in U.S. Pat. No. 8,013,154, the contents of which were incorporated herein above by reference in their entirety). This reaction was stirred at ambient temperature overnight. TLC indicated the reaction was complete. The solvent was removed under reduced pressure and the residue was purified using normal phase chromatography which afforded product (471 mg, 56% over three steps) as an off-white solid, mp 99-101° C.: Rf=0.26 (30% EtOAc, hex); 1H NMR (DMSO-d6) 10.34 (s, 1H), 7.48 (d, 1H, J=3.3 Hz), 6.78 (d, 1H, J=4.3 Hz), 6.28 (s, 1H), 5.02 (q, 4H, J=17.8, 8.9 Hz), 3.49 (s, 3H); ESIMS m/z 497 [(M-1)+].

Aufarbeitung

  1. customprepared
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified
  4. customafforded product (471 mg, 56% over three steps) as an off-white solid, mp 99-101° C.

Quellen und Nachweise

ORD-Eintrag
ord-0d3442196c7047669393b14f77310353
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227957B2

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