Triethylamine → HCID 11976939, compound

HRID 1808292Notes

Reaction equation

HRID 1808292 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.C(N(CC)CC)C.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([S:31](Cl)(=[O:33])=[O:32])[CH:26]=1>ClCCl>[OH:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][C:3]2([CH2:2][NH:1][S:31]([C:27]3[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=3)(=[O:33])=[O:32])[CH2:4][CH2:5][CH2:6][CH2:7]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3164136Pyridine-3-sulfonyl chlorideHCID 18999517HCID 18999517, compound

Product 1

HCID 11976939HCID 11976939, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 300 mg (1.086 mmol) of 2-(4-{[1-(aminomethyl)-cyclo-pentyl]methyl}phenyl)ethanol (EP 472 449), 30 ml of dichloromethane and 537.6 μl (3.857 mmol) of triethylamine is added dropwise, at −20° C., a solution of 310.1 mg (1.222 mmol) of 3-pyridinesulfonyl chloride in 10 ml of dichloromethane. The mixture is allowed to warm to room temperature slowly (over 3 hours) and is stirred for a further 2 hours. The reaction medium is then washed with water and dried over Na2SO4. After concentrating the organic phase under vacuum, the oil obtained is purified by flash chromatography on silica gel with a dichloromethane/methanol mixture (99/1). 266 mg of an amorphous white solid are obtained.

Workup

  1. additionis added dropwise, at −20° C.
  2. washThe reaction medium is then washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentrating the organic phase under vacuum
  5. customthe oil obtained
  6. customis purified by flash chromatography on silica gel with a dichloromethane/methanol mixture (99/1)

Sources & evidence

ORD record
ord-303942fa57144220887564a6741dc8d4
Source dataset
uspto-grants-2013_01
Patent number
US08357721B2

Reaction notes

Loading…