Ethylene Glycol → 4-[4-[(6,8-Dichloroimidazo[1,2-a]pyridin-2-yl)methyl]-1-piperazinyl]benzamide

HRID 1416264Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([Cl:13])[C:5]2[N:6]([CH:8]=[C:9]([CH2:11]Cl)[N:10]=2)[CH:7]=1.[N:14]1([C:20]2[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][CH:21]=2)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(N(CC)CC)C.C(O)CO>O>[Cl:1][C:2]1[CH:3]=[C:4]([Cl:13])[C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:17]3[CH2:16][CH2:15][N:14]([C:20]4[CH:21]=[CH:22][C:23]([C:24]([NH2:26])=[O:25])=[CH:27][CH:28]=4)[CH2:19][CH2:18]3)[N:10]=2)[CH:7]=1

Participants

Conditions

Temperature: 82.5 °C

Procedure

A mixture of 6,8-dichloro-2-(chloromethyl)imidazo[1,2-a]pyridine (Example 19, Step 1; 0.301 g), 4-(piperazin-1-yl)benzamide (Example 3, Step 1; 0.2916 g), triethylamine (Aldrich; 0.21 mL), and ethylene glycol (2 mL) is stirred for 1 h at 80-85° C. The mixture is then allowed to cool and water is added. The solids are collected, washed with water and hexane, and dried under reduced pressure. The solid is then adsorbed onto silica gel and chromatographed using methanol/dichloromethane (8/92). The appropriate fractions are combined and concentrated and the residue is crystallized from dichloromethane/methanol to give 0.2938 g of the title compound; mp 234-235° C.; MS m/z 403,405; IR (mineral oil) 1606, 1668, 1392, 1522, 1241 cm-1 ; 1H NMR (CDCl3) δ2.74, 3.35, 3.83, 6.89, 7.27, 7.63, 7.72, 8.10.

Workup

temperatureto cool
customThe solids are collected
washwashed with water and hexane
customdried under reduced pressure
customchromatographed
concentrationconcentrated
customthe residue is crystallized from dichloromethane/methanol

Sources & evidence

ORD record: ord-9014f093986145f1ad133d5b3a7ce58a
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05912246

Reaction notes

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