3-Amino-1,2-propanediol → N-(2,3-dihydroxypropyl)-2-fluoro-4-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzamide

HRID 2410581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2410581
[F:1][C:2]1[CH:10]=[C:9]([C:11]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[CH3:28])=[C:18]([CH2:29][O:30][CH3:31])[CH:17]=3)[O:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].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.[NH2:65][CH2:66][CH:67]([OH:70])[CH2:68][OH:69]>CN(C=O)C.CCOC(C)=O>[OH:70][CH:67]([CH2:68][OH:69])[CH2:66][NH:65][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][C:9]([C:11]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[CH3:28])=[C:18]([CH2:29][O:30][CH3:31])[CH:17]=3)[O:13][N:12]=2)=[CH:10][C:2]=1[F:1]

Komponenten

7

Edukt 4

HCID 735613-Amino-1,2-propanediolHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 252563812-Fluoro-4-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoic acid

Produkt 1

HCID 58066379N-(2,3-dihydroxypropyl)-2-fluoro-4-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Fluoro-4-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoic acid (75 mg, 0.18 mmol) was dissolved in anhydrous DMF (1 mL). N-ethyldiisopropylamine (65 μl, 0.38 mmol) was added followed by HATU (72 mg, 0.19 mmol) and the reaction was stirred at RT for 15 minutes. 3-Amino-1,2-propanediol (17 mg, 0.19 mmol) was added and the reaction stirred at RT overnight. EtOAc was added and the organic phase was washed three times with a 1N aqueous solution of HCl and brine. It was dried on MgSO4, filtered and concentrated. It was purified on preparative HPLC to afford the title compound as a brown solid. LC/MS (Method B): 492.2 (M+H)+, 490.3 (M−H)−. HPLC (Method A) Rt 4.82 min (Purity: 95.9%).

Aufarbeitung

  1. stirringthe reaction stirred at RT overnight
  2. washthe organic phase was washed three times with a 1N aqueous solution of HCl and brine
  3. customIt was dried on MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customIt was purified on preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-32316524c9e84798953e74ca6624e5ce
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815919B2

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