N,N-Dipropylethylamine → HCID 71280448, Verbindung

HRID 1497855

Reaktionsgleichung

Reaktionsgleichung von HRID 1497855
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:25]=[C:26]1[CH2:29][CH:28]([C:30]([OH:32])=O)[CH2:27]1.N(CC)(CCC)CCC.O[N:43]=[C:44]([C:46]1[CH:47]=[CH:48][C:49]([CH3:64])=[C:50]([NH:52][C:53]([C:55]2[N:59]3[CH:60]=[CH:61][CH:62]=[CH:63][C:58]3=[N:57][CH:56]=2)=[O:54])[CH:51]=1)[NH2:45]>CN(C=O)C>[CH3:64][C:49]1[CH:48]=[CH:47][C:46]([C:44]2[N:43]=[C:30]([CH:28]3[CH2:27][C:26](=[O:25])[CH2:29]3)[O:32][N:45]=2)=[CH:51][C:50]=1[NH:52][C:53]([C:55]1[N:59]2[CH:60]=[CH:61][CH:62]=[CH:63][C:58]2=[N:57][CH:56]=1)=[O:54]

Komponenten

6

Edukt 4

HCID 519799N,N-DipropylethylamineHCID 49133583-Oxocyclobutane-1-carboxylic acidHCID 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-carboxamide

Produkt 1

HCID 71280448HCID 71280448, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

HATU (1.41 g, 3.72 mmol) was added in one portion to a stirred solution of 3-oxocyclobutanecarboxylic acid (0.405 g, 3.55 mmol) and Pr2NEt (0.62 mL, 3.7 mmol) in dry DMF (5 mL). After 10 minutes, N-(5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (9) (1.0 g, 3.23 mmol) was added in one portion and continued to stir for another 30 minutes. The resulting solution was heated (110° C.) for 30 minutes and then cooled to room temperature. The solvent was evaporated and the residue was partitioned with saturated NH4Cl and EtOAc. The organic layer was dried with MgSO4 and filtered. The residue was purified on silica gel using 10% MeOH in dichloromethane to obtain N-(2-methyl-5-(5-(3-oxocyclobutyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide (10). 1H NMR (400 MHz, d6-DMSO) δ 10.20 (s, 1 H), 9.53-9.51 (m, 1 H), 8.71 (s, 1 H), 8.08 (d, J=1.6 Hz, 1 H), 7.91-7.88 (m, 1 H), 7.85 (dd, J=2.0, 8.0 Hz, 1 H), 7.72-7.68 (m, 1 H), 7.51 (d, J=8.4 Hz, 1 H), 7.34-7.30 (m, 1 H), 4.12-4.04 (m, 1 H), 3.70-3.53 (m, 4 H), 2.37 (s, 3 H). MS m/z 388.1 (M+1)+.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customThe solvent was evaporated
  3. customthe residue was partitioned with saturated NH4Cl and EtOAc
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. customThe residue was purified on silica gel using 10% MeOH in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-b8a87f3c174741268d93bcd17fc20525
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199981B2

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