Isopropanol → Methyl 3-(3-{2-[(3-{[2-(dimethylamino)ethyl]oxy}-2-methylphenyl)amino]-4-pyrimidinyl}imidazo[1,2-a]pyridin-2-yl)benzoate

HRID 419323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419323
Cl[C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]3=[N:10][C:9]=2[C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=2)[C:20]([O:22][CH3:23])=[O:21])[CH:5]=[CH:4][N:3]=1.[NH2:27][C:28]1[C:29]([CH3:39])=[C:30]([O:34][CH2:35][CH2:36][NH:37][CH3:38])[CH:31]=[CH:32][CH:33]=1.[CH3:40]C(O)C>Cl.C(Cl)Cl>[CH3:38][N:37]([CH3:40])[CH2:36][CH2:35][O:34][C:30]1[C:29]([CH3:39])=[C:28]([NH:27][C:2]2[N:7]=[C:6]([C:8]3[N:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]4=[N:10][C:9]=3[C:17]3[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=3)[C:20]([O:22][CH3:23])=[O:21])[CH:5]=[CH:4][N:3]=2)[CH:33]=[CH:32][CH:31]=1

Komponenten

6

Edukt 3

HCID 3776IsopropanolHCID 59452862Methyl 3-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]benzoateHCID 66649996{2-[(3-Amino-2-methylphenyl)oxy]ethyl}methylamine

Produkt 1

HCID 59452717Methyl 3-(3-{2-[(3-{[2-(dimethylamino)ethyl]oxy}-2-methylphenyl)amino]-4-pyrimidinyl}imidazo[1,2-a]pyridin-2-yl)benzoateAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A microwave vial was charged with methyl 3-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]benzoate (Intermediate Example 3) (1.75 g, 4.79 mmol), {2-[(3-amino-2-methylphenyl)oxy]ethyl}methylamine (863 mg, 4.79 mmol), iPrOH (10 mL) and 1 drop HCl, and the reaction mixture was stirred in a microwave reactor at 140° C. for 30 min. The mixture was diluted with DCM and quenched with saturated NaHCO3. The organics were separated, dried over MgSO4, and the solvent was removed. The crude material was purified via silica gel chromatography to give 1.70 g (68% yield) of the title compound. MS (APCI+) m/z 523 [M+H].

Aufarbeitung

  1. customquenched with saturated NaHCO3
  2. customThe organics were separated
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed
  5. customThe crude material was purified via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cba4ee697e50470aa00d2a523bc7306c
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

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