Diisopropylethylamine → N-(5-(5-(5,5-difluorotetrahydro-2H-pyran-2-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 570353

Reaktionsgleichung

Reaktionsgleichung von HRID 570353
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:25][C:26]1([F:35])[CH2:31][O:30][CH:29]([C:32]([OH:34])=O)[CH2:28][CH2:27]1.CCN(C(C)C)C(C)C.O[N:46]=[C:47]([C:49]1[CH:50]=[CH:51][C:52]([CH3:67])=[C:53]([NH:55][C:56]([C:58]2[N:62]3[CH:63]=[CH:64][CH:65]=[CH:66][C:61]3=[N:60][CH:59]=2)=[O:57])[CH:54]=1)[NH2:48]>CN(C=O)C>[F:35][C:26]1([F:25])[CH2:31][O:30][CH:29]([C:32]2[O:34][N:46]=[C:47]([C:49]3[CH:50]=[CH:51][C:52]([CH3:67])=[C:53]([NH:55][C:56]([C:58]4[N:62]5[CH:63]=[CH:64][CH:65]=[CH:66][C:61]5=[N:60][CH:59]=4)=[O:57])[CH:54]=3)[N:48]=2)[CH2:28][CH2:27]1

Komponenten

6

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 86677441N-(5-(N'-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamideHCID 866774605,5-Difluorooxane-2-carboxylic acid

Produkt 1

HCID 71280797N-(5-(5-(5,5-difluorotetrahydro-2H-pyran-2-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

HATU (0.134 g, 0.355 mmol) was added in one portion to a stirred solution of 5,5-difluorotetrahydro-2H-pyran-2-carboxylic acid (17) (53 mg, 0.31 mmol) and DIEA (60 L, 0.355 mmol) in dry DMF (3 mL). After 10 minutes, N-(5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (9) (0.1 g, 0.323 mmol) was added in one portion and continued to stir for another 30 minutes, then heated at 110° C. for 30 minutes. The reaction was filtered and purified by preparative reverse phase HPLC to afford N-(5-(5-(5,5-difluorotetrahydro-2H-pyran-2-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F10) as a white solid. 1H NMR (400 MHz, d4-MeOH) δ 9.73 (d, J=7.2 Hz, 1H), 8.74 (s, 1H), 8.17 (m, 1H), 7.98-7.95 (m, 3H), 7.52-7.50 (m, 2H), 5.06 (dd, J=8.4, 2.8 Hz, 1H), 4.07-4.00 (m, 1H), 3.91-3.81 (m, 1H), 2.44 (s, 3H), 2.40-2.21 (m, 4H). MS m/z 440.1 (M+1)+.

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. custompurified by preparative reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-35627eea05b04ecca1294954e9e9c54b
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023839B2

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