Pyridine → HCID 59482958, compound

HRID 1255388Notes

Reaction equation

HRID 1255388 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][C:7](=[O:13])[CH:6]=[C:5]2[CH2:14][C:15]([NH:17][CH2:18][CH2:19][N:20]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH3:21])=[O:16].[C:32](OC(=O)C)(=[O:34])[CH3:33].N1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:32](=[O:34])[CH3:33])[O:8][C:7](=[O:13])[CH:6]=[C:5]2[CH2:14][C:15]([NH:17][CH2:18][CH2:19][N:20]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH3:21])=[O:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86645271HCID 86645271, compound

Product 1

HCID 59482958HCID 59482958, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A sample of this 2-(6-Chloro-7-hydroxycoumarin-4-yl)-N-[2-(N-decyl-N-methyl-amino)ethyl]acetamide (26 mg, 0.06 mmole) was dissolved in anhydrous dichloromethane (5 mL) and acetic anhydride (0.5 mL, 5.3 mmole) and dry pyridine (0.5 mL, 6.2 mmole) added. This mixture was allowed to stir overnight, and the resulting solution, diluted with dichloromethane (30 mL) and extracted with water (1×25 mL), saturated sodium bicarbonate solution (1×25 mL), 1N HCl (1×25 mL) and water (1×25 mL). The resulting dichloromethane layer was dried over anhydrous sodium sulfate, filtered and evaporated. Drying in vacuo provided an off-white solid (22 mg, 79%). A biocompatible solution of this substrate was prepared by dissolving 22 mg in dry DMSO (0.446 mL) for staining live cells for esterase activity.

Workup

  1. extractionextracted with water (1×25 mL), saturated sodium bicarbonate solution (1×25 mL), 1N HCl (1×25 mL) and water (1×25 mL)
  2. dry with materialThe resulting dichloromethane layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customDrying in vacuo

Sources & evidence

ORD record
ord-9edba08355a04f93bfcb7372a19f45a9
Source dataset
uspto-grants-2013_06
Patent number
US08460862B2

Reaction notes

Loading…