1-Methylcyclopropanecarboxylic acid → HCID 44200545, Verbindung

HRID 2061166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2061166
[CH3:1][C:2]1([C:5]([OH:7])=O)[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:41][N:42]1[C:51]2[C:46](=[CH:47][N:48]=[C:49]([CH3:52])[CH:50]=2)[CH:45]=[C:44]([C:53]2[CH:54]=[C:55]([NH:60]/[C:61](/[NH2:64])=[N:62]/O)[CH:56]=[CH:57][C:58]=2[CH3:59])[C:43]1=[O:65]>CN(C=O)C>[CH3:41][N:42]1[C:51]2[C:46](=[CH:47][N:48]=[C:49]([CH3:52])[CH:50]=2)[CH:45]=[C:44]([C:53]2[CH:54]=[C:55]([NH:60][C:61]3[N:62]=[C:5]([C:2]4([CH3:1])[CH2:4][CH2:3]4)[O:7][N:64]=3)[CH:56]=[CH:57][C:58]=2[CH3:59])[C:43]1=[O:65]

Komponenten

6

Edukt 4

HCID 813261-Methylcyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178422078HCID 178422078, Verbindung2×

Produkt 1

HCID 44200545HCID 44200545, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 1-methylcyclopropanecarboxylic acid (6 mg, 0.06 mmol) in DMF (1 mL) were added DIPEA (31 μL, 0.18 mmol) and HATU (23 mg, 0.06 mmol). After stirring at rt for 15 min, 17 (20 mg, 0.06 mmol) was added as a solution in DMF (0.5 mL). The reaction was stirred at rt until complete consumption of 17 was determined by LC/MS and then heated at 100° C. for 1 h. Subsequently the reaction was cooled to rt, filtered and purified by preparative LC/MS to give 1,7-dimethyl-3-(2-methyl-5-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one (A34) as an off white solid. 1H NMR (400 MHz, d6-DMSO) δ 9.87 (s, 1H), 9.13 (s, 1H), 8.05 (s, 1H), 7.87 (s, 1H), 7.37 (dd, J=8, 2 Hz, 1H), 7.30 (d, J=2 Hz, 1H), 7.22 (d, J=8 Hz, 2H), 3.70 (s, 3H), 2.75 (s, 3H), 2.07 (s, 3H), 1.47 (s, 3H), 1.27 (m, 2H), 1.08 (m, 2H). MS m/z 402.4 (M+1).

Aufarbeitung

  1. temperatureheated at 100° C. for 1 h
  2. temperatureSubsequently the reaction was cooled to rt
  3. filtrationfiltered
  4. custompurified by preparative LC/MS

Quellen und Nachweise

ORD-Eintrag
ord-7b56d2ea90594499b62347b6caeef74b
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278452B2

Notizen zur Reaktion

Wird geladen…