Triethylamine → 3-[4-(Azetidin-1-ylcarbonyl)-3-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 20605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20605
[N:1]1([C:5]([C:7]2[CH:33]=[CH:32][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:31])[CH2:29][OH:30])[CH:26]=3)[C:15]([NH:17][C:18]3[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=3)=[O:16])=[C:9](Cl)[C:8]=2[F:35])=[O:6])[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C>CO>[N:1]1([C:5]([C:7]2[CH:33]=[CH:32][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:31])[CH2:29][OH:30])[CH:26]=3)[C:15]([NH:17][C:18]3[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=3)=[O:16])=[CH:9][C:8]=2[F:35])=[O:6])[CH2:2][CH2:3][CH2:4]1

Komponenten

4

Edukt 2

HCID 8471TriethylamineHCID 115842233-[4-(Azetidin-1-ylcarbonyl)-2-chloro-3-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Produkt 1

HCID 116557263-[4-(Azetidin-1-ylcarbonyl)-3-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamideAusbeute 39,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3-[4-(Azetidin-1-ylcarbonyl)-2-chloro-3-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (162 mg; 0.322 mmol) was dissolved in methanol (10 mL). Triethylamine (97 mg, 0.967 mmol) was added and the flask evacuated and purged with nitrogen (3 times). 10% Palladium on carbon (25 mg) was added and the flask further evacuated and finally purged with hydrogen gas. The reaction mixture was stirred at ambient temperature for 7 days until completion. The reaction mixture was evacuated and purged with nitrogen (3 times). The catalyst was filtered off, the filtrate concentrated in vacuo and purified by preparatory reverse phase HPLC using a gradient of 5-95% acetonitrile in water (containing 0.2% TFA) on a Phenomenex Luna 10u C18 (2) 100A column to give the title compound (60 mg).

Aufarbeitung

  1. customthe flask evacuated
  2. custompurged with nitrogen (3 times)
  3. addition10% Palladium on carbon (25 mg) was added
  4. customthe flask further evacuated
  5. customfinally purged with hydrogen gas
  6. customThe reaction mixture was evacuated
  7. custompurged with nitrogen (3 times)
  8. filtrationThe catalyst was filtered off
  9. concentrationthe filtrate concentrated in vacuo
  10. custompurified by preparatory reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-abfb473692b4426a8e343784496fa7ca
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745475B2

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