Triethylamine → HCID 10622474, compound

HRID 636494Notes

Reaction equation

HRID 636494 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][CH2:16][C:17]([N:19]([C:21]2[C:22]([CH3:30])=[C:23]([CH2:28]O)[C:24]([CH3:27])=[CH:25][CH:26]=2)[CH3:20])=[O:18])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.S([Cl:42])(C)(=O)=O.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(Cl)(Cl)Cl>[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][CH2:16][C:17]([N:19]([C:21]2[C:22]([CH3:30])=[C:23]([C:24]([CH3:27])=[CH:25][CH:26]=2)[CH2:28][Cl:42])[CH3:20])=[O:18])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 10692926HCID 10692926, compound

Product 1

HCID 10622474HCID 10622474, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[N-[(E)-3-(6-acetylaminopyridin-3-yl)acryloylglycyl]-N-methylamino]-1-hydroxymethyl-2,6-dimethylbenzene (200 mg) in dimethylformamide (2 ml) were added triethylamine (136.1 μl) and mesyl chloride (52.9 μl) at 0° C., and the mixture was stirred for 1 hour at the same temperature and then for 1 hour at ambient temperature. Chloroform and saturated sodium bicarbonate solution were added to the reaction mixture, and the separated organic layer was washed with water, saturated sodium bicarbonate solution and brine, and dried over magnesium sulfate. The solvent was removed in vacuo to give 3-[N-[(E)-3-(6-acetylaminopyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dimethylbenzyl chloride (191.0 mg) as pale yellow solid.

Workup

  1. waitfor 1 hour at ambient temperature
  2. washthe separated organic layer was washed with water, saturated sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-46ab79bff5494d2fb3c90faa20776aa6
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

Loading…