Ethyl chloroformate → Ethyl 3-(6-methyl-2-(1-(6-methylpyrimidin-4-yl)piperidin-4-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-yl)benzylcarbamate

HRID 451487Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451487
Cl.Cl.[NH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:11]2[C:12]3[N:13]([N:18]=[C:19]([NH:21][CH:22]4[CH2:27][CH2:26][N:25]([C:28]5[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30][N:29]=5)[CH2:24][CH2:23]4)[N:20]=3)[CH:14]=[C:15]([CH3:17])[CH:16]=2)[CH:8]=[CH:9][CH:10]=1.C(N(CC)C(C)C)(C)C.Cl[C:45]([O:47][CH2:48][CH3:49])=[O:46]>ClCCl>[CH3:17][C:15]1[CH:16]=[C:11]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[CH2:4][NH:3][C:45](=[O:46])[O:47][CH2:48][CH3:49])[C:12]2[N:13]([N:18]=[C:19]([NH:21][CH:22]3[CH2:23][CH2:24][N:25]([C:28]4[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30][N:29]=4)[CH2:26][CH2:27]3)[N:20]=2)[CH:14]=1

Komponenten

5

Edukt 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 67342484HCID 67342484, Verbindung

Produkt 1

HCID 67344382Ethyl 3-(6-methyl-2-(1-(6-methylpyrimidin-4-yl)piperidin-4-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-yl)benzylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of 8-(3-(aminomethyl)phenyl)-6-methyl-N-(1-(6-methylpyrimidin-4-yl)piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine dihydrochloride (37 mg, 73.8 μmol) in dichloromethane (0.75 mL) was added N,N-diisopropylethylamine (38.1 mg, 51.5 μL, 295 mmol). To the resulting yellow solution was added ethyl chloroformate (8.99 mg, 7.89 μL, 81.2 mmol) and the reaction was stirred at room temperature over night. The title compound was obtained as a light yellow solid (35 mg, 95%) after column chromatography on silica gel using a gradient from methylene chloride to a mixture of methylene chloride/methanol 19:1 (v/v) as eluent. MS ISP (m/e): 501.2 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): (ppm)=8.51 (s, 1H), 8.13 (s, 1H), 7.83 (br s, 2H), 7.44 (t, 1H), 7.36 (s, 1H), 7.33 (d, 1H), 6.41 (s, 1H), 5.08 (br m, 1H), 4.53 (br d, 1H), 4.44 (d, 2H), 4.32 (br d, 2H), 4.15 (q, 2H), 3.96 (m, 1H), 3.69 (m, 1H), 3.20 (t, 2H), 3.10 (m, 1H), 2.40 (s, 3H), 2.38 (s, 3H), 2.22 (br d, 2H), 1.25 (t, 3H).

Quellen und Nachweise

ORD-Eintrag
ord-eae6533b9e7842a3bed86d1d47002113
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486967B2

Notizen zur Reaktion

Wird geladen…