(2-Amino-5-methyl-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester → 4-[3-(4-Hydroxymethyl-thiazol-2-yl)-phenyl]-7-methyl-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1266899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1266899
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=1[NH2:19])(C)(C)C.C(O[C:26](=[O:49])[CH2:27][C:28](=O)[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]2[S:36][CH:37]=[C:38]([CH2:40][O:41]C3CCCCO3)[N:39]=2)[CH:30]=1)(C)(C)C>C1(C)C=CC=CC=1>[OH:41][CH2:40][C:38]1[N:39]=[C:35]([C:31]2[CH:30]=[C:29]([C:28]3[CH2:27][C:26](=[O:49])[NH:19][C:9]4[CH:10]=[C:11]([C:15]([F:16])([F:17])[F:18])[C:12]([CH3:14])=[CH:13][C:8]=4[N:7]=3)[CH:34]=[CH:33][CH:32]=2)[S:36][CH:37]=1

Komponenten

4

Edukt 2

HCID 67361461(2-Amino-5-methyl-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl esterHCID 696884923-Oxo-3-[3-[4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-2-yl]-phenyl]-propionic acid tert-butyl ester

Produkt 1

HCID 185488054-[3-(4-Hydroxymethyl-thiazol-2-yl)-phenyl]-7-methyl-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-oneAusbeute 18,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of (2-amino-5-methyl-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (Example J15) (0.145 g) and 3-oxo-3-[3-[4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-2-yl]-phenyl]-propionic acid tert.-butyl ester (Example K19) (0.23 g) in toluene (2 mL) was heated to 100° C. for 5 h. The mixture was cooled and evaporated in vacuum. A solution of the residue in a mixture of CH2Cl2 (2 mL) and TFA (2 mL) was stirred for 0.5 h at 20° C. The mixture was evaporated in vacuum, the residual oil was dissolved in AcOEt and the solution was washed with saturated NaHCO3 solution and with brine, dried over Na2SO4 and evaporated in vacuum. The residue was crystallized from CH2Cl2/hexane to give the title compound (0.04 g) as light-brown crystals.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. customevaporated in vacuum
  3. additionA solution of the residue in a mixture of CH2Cl2 (2 mL) and TFA (2 mL)
  4. customThe mixture was evaporated in vacuum
  5. dissolutionthe residual oil was dissolved in AcOEt
  6. washthe solution was washed with saturated NaHCO3 solution and with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated in vacuum
  9. customThe residue was crystallized from CH2Cl2/hexane

Quellen und Nachweise

ORD-Eintrag
ord-29bf553dee7d4bea884891e36531f6e2
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06548495B2

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