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

HRID 419323Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

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].

Workup

customquenched with saturated NaHCO3
customThe organics were separated
dry with materialdried over MgSO4
customthe solvent was removed
customThe crude material was purified via silica gel chromatography

Sources & evidence

ORD record: ord-cba4ee697e50470aa00d2a523bc7306c
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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