Triethylamine → HCID 22507062, compound

HRID 985484Notes

Reaction equation

HRID 985484 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([O:11][CH2:10][CH2:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:2][CH3:1])[N:8]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 105348582-[6-(Methylamino)-2-pyridyl]ethan-1-ol

Product 1

HCID 22507062HCID 22507062, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 2-[6-(Methylamino)-2-pyridyl]ethan-1-ol (300 mg, 1.9 mmol), triethylamine (0.3 ml, 2.2 mmol), methanesulfonyl chloride (0.17 ml, 2.2 mmol), and dichloromethane (15 ml) was stirred at 0° C. for 30 minutes. The reaction mixture was diluted with dichloromethane and washed with water. The organic layer was dried with sodium sulfate, filtered, and evaporated under vacuum to give a yellow oil. The crude product was chromatographed over silica gel to yield 300 mg (69%) of 2-[6-(Methylamino)-2-pyridyl]ethyl methylsulfonate. NMR 1H Cl3CD δ: 7.45 (dd, 1H, J=7.2, 8.4 Hz), 6.51 (d, 1H, J=7.2 Hz), 6.33 (d, 1H, J=8.4 Hz), 4.65 (t, 2H, J=6.4 Hz), 3.06 (t, 2H, J=6.4 Hz), 2.92 (m, 6H).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customto give a yellow oil
  6. customThe crude product was chromatographed over silica gel

Sources & evidence

ORD record
ord-1d9cb3f092ae43489e8d534046eb3c05
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

Loading…