Ethylene Glycol → HCID 15409147, compound

HRID 1416242Notes

Reaction equation

HRID 1416242 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:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)CC)C.C(O)CO>O>[N:4]1[C:3]([CH2:2][N:15]2[CH2:16][CH2:17][N:12]([C:18]3[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[CH2:13][CH2:14]2)=[CH:11][N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=12

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 8471TriethylamineHCID 9018974-(Piperazin-1-yl)benzene-1-sulfonamideHCID 9576142-Chloromethyl-imidazo(1,2-A)pyridine

Product 1

HCID 15409147HCID 15409147, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(chloromethyl)imidazo[1,2-a]pyridine (0.495 g), 4-(piperazin-1-yl) benzenesulfonamide (0.717 g), triethylamine (0.456 mL), and ethylene glycol (6 mL) is stirred at 80° C. for 1.5 h. After cooling, water is added and the resulting solid is collected and washed with water and toluene. Chromatography on silica gel using methanol/dichloromethane (6/94) yields 0.69 g of the title compound; mp 238-242° C.; IR (mineral oil) 1150, 1152, 1331, 1308, 1508 cm-1. 1H NMR (DMSOd6) δ2.61. 3.28, 3.66, 6.86, 7.02, 7.06, 7.20, 7.49, 7.61, 7.85, 8.50.

Workup

  1. temperatureAfter cooling
  2. customthe resulting solid is collected
  3. washwashed with water and toluene

Sources & evidence

ORD record
ord-4bdd1040c5ca4266a1b85f5afa148947
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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