Diisopropylethylamine → HCID 15409148, compound

HRID 1416244Notes

Reaction equation

HRID 1416244 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]2[CH:11]=1.[N:12]1([C:18]2[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[CH:20][CH:19]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(C(C)C)CC)(C)C>C(O)CO>[N:4]1[C:3]([CH2:2][N:15]2[CH2:14][CH2:13][N:12]([C:18]3[CH:19]=[CH:20][C:21]([C:22]([NH2:24])=[O:23])=[CH:25][CH:26]=3)[CH2:17][CH2:16]2)=[CH:11][N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=12

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9576142-Chloromethyl-imidazo(1,2-A)pyridineHCID 111065094-(1-Piperazinyl)benzamide

Product 1

HCID 15409148HCID 15409148, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Following the general procedure of Example 2, Step 3, and making noncritical variations, 2-(chloromethyl)imidazo[1,2-a]pyridine (Example 2, Step 1; 0.245 g), 4-(piperazin-1-yl)benzamide (0.302 g), diisopropylethylamine (Aldrich; 0.256 mL), and ethylene glycol (2 mL) gives 0.313 g of the title compound after chromatography (silica gel, methanol/dichloromethane, 8/92, as eluent) and crystallization from methanol/dichloromethane; mp 249-250° C.; IR (mineral oil) 1608, 1398, 1253, 1739, 3133, 756 cm-1. 1H NMR (CDCl3) δ2.74, 3.36, 3.78, 5.7, 6.78, 6.88, 7.16, 7.55, 7.58, 7.71, 8.09.

Sources & evidence

ORD record
ord-453d766e78a647a5ba0295f51a00025d
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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