Diisopropylethylamine → 4-benzyloxy-N-[3-tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-2-fluoro-benzamide

HRID 2390875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2390875
[C:1]([C:5]1[C:6]([O:20][CH3:21])=[C:7]([NH2:19])[CH:8]=[C:9]([C:11]2[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:22]([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][C:31]=1F)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[F:57][P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>O.CN(C=O)C>[CH2:22]([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:19][C:7]2[CH:8]=[C:9]([C:11]3[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=3)[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6]=2[O:20][CH3:21])=[O:35])=[C:32]([F:57])[CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 187575074-Benzyloxy-3-fluorobenzoic acidHCID 670698823-Tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenylamine

Produkt 1

HCID 670699134-benzyloxy-N-[3-tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-2-fluoro-benzamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

step 1—A solution of 100 (100 mg, 0.349 mmol, 4-benzyloxy-3-fluoro-benzoic acid (86 mg, 0.349 mmol), HATU (146 mg, 0.384 mmol, DIPEA (0.122 mL, 0.698 mmol), and DMF (3 mL) is stirred at 50° under Ar overnight. The reaction was cooled, diluted with H2O and extracted with EtOAc. The combined extracts were washed with H2O, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 eluting with 20% EtOAc/hexane to afford 0.125 g (85%) of 4-benzyloxy-N-[3-tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-2-fluoro-benzamide (322) which could be recrystallized from EtOAc.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with H2O
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by SiO2 eluting with 20% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-320bc3aaa98b474dae8c6d199fa38c53
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273773B2

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