Sodium Acetate → 5-(2-Amino-thiazol-4-yl)-6-methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

HRID 1888809

Reaktionsgleichung

Reaktionsgleichung von HRID 1888809
[CH3:1][S:2]([C:5]1[CH:36]=[CH:35][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:14](=[O:34])[N:15]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)[C:16]([CH3:23])=[C:17]([C:19](=O)[CH2:20]Br)[CH:18]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH2:37][C:38]([NH2:40])=[S:39].CC([O-])=O.[Na+]>CCO>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:14](=[O:34])[N:15]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:31])[F:32])[CH:25]=3)[C:16]([CH3:23])=[C:17]([C:19]3[N:37]=[C:38]([NH2:40])[S:39][CH:20]=3)[CH:18]=2)=[O:12])=[CH:35][CH:36]=1)(=[O:3])=[O:4]

Komponenten

5

Edukt 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 866147805-(bromoacetyl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

Produkt 1

HCID 866147815-(2-Amino-thiazol-4-yl)-6-methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamideAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

5-Bromoacetyl-6-methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide (Example 50 (c), 0.04 g, 0.067 mmol), thiourea (0.0067 g, 0.086 mmol), NaOAc (0.011 g, 0.136 mmol), EtOH (2 ml) and a magnetic stirrer bar were placed in a tube designed for microwave synthesis. The vial was sealed and the mixture was heated in a CEM Discover Microwave apparatus (100 W, 90° C.) for 20 minutes, giving complete conversion of the starting material to a single product according to LC-MS. The solvents were evaporated to give a crude mixture which was purified on preparative HPLC giving the title compound (0.026 g, 66%) as a slightly yellowish solid after freeze-drying the pure fractions.

Aufarbeitung

  1. customdesigned for microwave synthesis
  2. customThe vial was sealed
  3. customgiving complete conversion of the starting material to a single product
  4. customThe solvents were evaporated
  5. customto give a crude mixture which
  6. customwas purified on preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-1b3fe496dde14a2dab76905d463a6b62
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501784B2

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