Ethylene Glycol → HCID 54217619, compound

HRID 1416248Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][N:6]2[CH:12]=1.[N:13]1([C:19]2[CH:27]=[CH:26][C:22]([C:23]([NH2:25])=[O:24])=[CH:21][CH:20]=2)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(CC)CC)C.C(O)CO>O>[CH3:11][C:9]1[CH:8]=[CH:7][N:6]2[CH:12]=[C:3]([CH2:2][N:16]3[CH2:15][CH2:14][N:13]([C:19]4[CH:20]=[CH:21][C:22]([C:23]([NH2:25])=[O:24])=[CH:26][CH:27]=4)[CH2:18][CH2:17]3)[N:4]=[C:5]2[CH:10]=1

Participants

Conditions

Temperature: 82.5 °C

Procedure

A mixture of 2-(chloromethyl)-7-methylimidazo[1,2-α]pyridine (Example 6, Step 1; 0.300 g), 4-(piperazin-1-yl)benzamide (Example 3, Step 1; 0.357 g), triethylamine (Aldrich; 0.26 mL), and ethylene glycol (2 mL) is stirred for 30 min at 80-85° C. Additional ethylene glycol (1 mL) is added and the mixture is stirred for another 1.5 h. Water (8 mL) is added to the cooled mixture and the resulting solid is collected and dried. This material is adsorbed to silica gel and chromatographed on silica gel using methanol/dichloromethane/ammonium hydroxide (8/92/0.5). The appropriate fractions are combined and concentrated and the residue is crystallized from ethyl acetate/methanol to give 0.211 g of the title compound; mp 217-218° C.; ms m/z 349; IR (mineral oil) 1608, 1662, 1239, 3393, 1520 cm-1 ; 1H NMR (CDCl3) δ2.39, 2.74. 3.35. 3.75, 6.60. 6.88, 7.32, 7.46, 7.70 7.95.

Workup

stirringthe mixture is stirred for another 1.5 h
customthe resulting solid is collected
customdried
customchromatographed on silica gel
concentrationconcentrated
customthe residue is crystallized from ethyl acetate/methanol

Sources & evidence

ORD record: ord-3a32ae75736b4d2ea515169b8f27e1cc
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05912246

Reaction notes

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