Triethylamine → HCID 15409150, compound

HRID 1416246Notes

Reaction equation

HRID 1416246 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11]Cl)[N:10]=2)[CH:7]=1.[N:13]1([C:19]2[CH:24]=[CH:23][C:22]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(CC)CC)C>C(O)CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:16]3[CH2:17][CH2:18][N:13]([C:19]4[CH:24]=[CH:23][C:22]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:21][CH:20]=4)[CH2:14][CH2:15]3)[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9018974-(Piperazin-1-yl)benzene-1-sulfonamideHCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine

Product 1

HCID 15409150HCID 15409150, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Following the general procedure of Example 2, Step 3, and making noncritical variations, 6-chloro-2-(chloromethyl)imidazo[1,2-a]pyridine (Example 4, Step 1; 0.500 g), 4-(piperazin-1-yl)benzenesulfonamide (Example 2, Step 2; 0.630 g), triethylamine (0.477 g), and ethylene glycol (6 mL) give 0.40 g of the title compound after chromatography on silica gel using methanol/dichloromethane (8/92) and crystallization from methanol/dichloromethane; mp 255-256° C.; IR (mineral oil) 1153, 1327, 1322, 3306, 1106 cm-1. 1H NMR (DMSOd6) δ2.60, 3.29, 3.66, 7.01, 7.06, 7.25, 7.54, 7.60, 7.84, 8.80.

Sources & evidence

ORD record
ord-84904565a7a645469f9302ab7f68cee9
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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