Water → N-(2-(4-Methoxyphenyl)ethyl)acetamide

HRID 352636

Reaktionsgleichung

NCCCN(C1C=C(C)N=C(N2C=CN=C2)N=1)[CH2:6][C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:8].O.[O-]C#N.[K+]>N1C=CC=CC=1>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][NH:9][C:7](=[O:8])[CH3:6])=[CH:17][CH:16]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To 2-[(3-aminopropyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]-N-[2-(4-methoxyphenyl)ethyl]acetamide (135 mg, 0.32 mmol) (a compound of formula (Yc6)) in pyridine (1.5 mL) was added water (1.5 mL) solution of potassium cyanate (64 mg, 0.76 mmol). The mixture was stirred and heated in an oil bath at 80° C. overnight. The mixture was poured into water and extracted with ethyl acetate (3×20 mL). The combined ethyl acetate fractions were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (9:1 CH3CN/NH4OH) to afford 2-[[3-ureido)propyl][2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]-N-[2-(4-methoxyphenyl)ethyl]acetamide, a compound of formula (Yc9); as a white solid; NMR (DMSO-d6, 90° C.) 8.4 (s, 1), 7.8 (s, 1), 7.05 (d, 2), 7.0 (s, 1), 6.75 (d, 2), 6.4 (s, 1), 4.1 (s, 2), 3.7 (s, 3), 3.5 (m, 2), 3.25 (m, 2), 3.05 (m, 2), 2.65 (t, 2), 2.3 (s, 3), 1.7 (m, 2) ppm.

Aufarbeitung

extractionextracted with ethyl acetate (3×20 mL)
washThe combined ethyl acetate fractions were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was purified by chromatography on silica gel (9:1 CH3CN/NH4OH)

Quellen und Nachweise

ORD-Eintrag: ord-4570b7c87a2f40b9b961f8ca69c3088e
Quelldatensatz: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06747031B2

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