Triethylamine → HCID 131732205, compound

HRID 1409359Notes

Reaction equation

HRID 1409359 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[CH:7]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C1COCC1>[CH3:23][S:24]([N:1]([C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[CH:7]=1)[S:24]([CH3:23])(=[O:26])=[O:25])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14925628Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 131732205HCID 131732205, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate (0.975 mmol, 0.2 g) was dissolved in THF (10 ml). Triethylamine (9.75 mmol, 0.986 g) was added and the mixture was cooled to 0° C. Methanesulfonyl chloride (9.75 mmol, 1.116 g) was slowly added and the mixture was allowed to cool to RT. The stirring continued at RT until the reaction was finished. The solvent was evaporated, DCM was added and washed with NaHCO3 solution and water. The organic phase was dried, filtered and evaporated. The crude product was purified with flash chromatography. 0.149 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.33 (t, 3H), 3.61 (s, 6H), 4.34 (q, 2H), 7.50 (dd, 1H), 7.69-7.74 (m, 1H), 8.54-8.56 (m, 1H), 9.00-9.02 (m, 1H).

Workup

  1. temperatureto cool to RT
  2. customcontinued at RT until the reaction
  3. customThe solvent was evaporated
  4. additionDCM was added
  5. washwashed with NaHCO3 solution and water
  6. customThe organic phase was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified with flash chromatography

Sources & evidence

ORD record
ord-2cbe17321b604d0dbd8b624f2cd70053
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

Loading…