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

HRID 1888814
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Reaktionsgleichung

Reaktionsgleichung von HRID 1888814
Br[CH:2]([CH3:37])[C:3]([C:5]1[CH:6]=[C:7]([C:23]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[C:8](=[O:22])[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:10]=1[CH3:11])=O.C([O:44][CH2:45][C:46]([NH2:48])=[S:47])(=O)C(C)(C)C>CCO>[CH3:36][S:33]([C:30]1[CH:31]=[CH:32][C:27]([CH2:26][NH:25][C:23]([C:7]2[C:8](=[O:22])[N:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:19])[F:21])[CH:13]=3)[C:10]([CH3:11])=[C:5]([C:3]3[N:48]=[C:46]([CH2:45][OH:44])[S:47][C:2]=3[CH3:37])[CH:6]=2)=[O:24])=[CH:28][CH:29]=1)(=[O:35])=[O:34]
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Komponenten

4

Edukt 2

HCID 27821132-Amino-2-thioxoethyl 2,2-dimethylpropanoateHCID 866147825-(2-bromopropanoyl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamide

Produkt 1

HCID 667254055-(2-Hydroxymethyl-5-methyl-thiazol-4-yl)-6-methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5-(2-Bromopropanoyl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (Example 53 (b), 0.06 g, 0.10 mmol), 2-amino-2-thioxoethyl pivalate (0.022 g, 0.125 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, 80° C.) for 40 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 silica giving 0.045 g (76%) of the intermediate pivalyl ester. This compound was dissolved in THF (2 ml) and water (2 ml). To this solution was added NaOH (0.2 mmol, 0.1 ml of a 2M solution), and the mixture was stirred at room temperature overnight. The THF was evaporated off and the water phase was acidified, extracted, and the extracts were evaporated. Purification by preparative HPLC gave pure fractions which were freeze-dried to give the title compound (0.040 g, 68%) as a white solid.

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 silica giving 0.045 g (76%) of the intermediate pivalyl ester
  7. dissolutionThis compound was dissolved in THF (2 ml)
  8. additionTo this solution was added NaOH (0.2 mmol, 0.1 ml of a 2M solution), and the mixture
  9. customThe THF was evaporated off
  10. extractionextracted
  11. customthe extracts were evaporated
  12. customPurification by preparative HPLC
  13. customgave pure fractions which
  14. customwere freeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-afe58edfb3c54873a1d2f9cd473727e0
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08501784B2

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