Diisopropylethylamine → Methyl 4-methoxy-3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoate

HRID 219956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219956
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:53][C:54](=[N:67]O)[C:55]1[CH:56]=[C:57]([CH:62]=[CH:63][C:64]=1[O:65][CH3:66])[C:58]([O:60][CH3:61])=[O:59]>CN(C=O)C>[CH3:66][O:65][C:64]1[CH:63]=[CH:62][C:57]([C:58]([O:60][CH3:61])=[O:59])=[CH:56][C:55]=1[C:54]1[N:53]=[C:10]([C:8]2[CH:7]=[CH:6][C:5]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])=[C:4]([CH2:3][O:2][CH3:1])[CH:9]=2)[O:12][N:67]=1

Komponenten

6

Edukt 4

HCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53410613Methyl 3-[amino(hydroxyimino)methyl]-4-methoxybenzoateHCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid

Produkt 1

HCID 59495740Methyl 4-methoxy-3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of Intermediate 28 (149.42 mg; 0.58 mmol) and n-ethyldiisopropylamine (198.29 μL; 1.17 mmol) in anhydrous DMF (2 mL) and cooled at 0° C., HATU (221.67 mg; 0.58 mmol) was added and the mixture stirred at RT for 10 min. After this time, Intermediate 53 (100 mg; 0.60 mmol) and DIEA (0.10 mL) in anhydrous DMF (1 mL) were added and the mixture was heated at 80° C. for 18 h. The reaction mixture was cooled to RT, partitioned between water and Et2O, dried over MgSO4, filtered and evaporated under vacuum. Product was adsorbed on silica and purified by flash chromatography (cHex/EtOAc from 9:1 to 8:2), which gave the title compound as a colorless oil. LC/MS (Method B): 445.2 (M+H)+. HPLC (Method A) Rt 6.01 min (purity: 96.5%).

Aufarbeitung

  1. temperaturethe mixture was heated at 80° C. for 18 h
  2. temperatureThe reaction mixture was cooled to RT
  3. custompartitioned between water and Et2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. custompurified by flash chromatography (cHex/EtOAc from 9:1 to 8:2), which

Quellen und Nachweise

ORD-Eintrag
ord-7e34afec57ed4bb4b2278f2b51a567f2
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202865B2

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