Pyridine → HCID 68814924, compound

HRID 1436664Notes

Reaction equation

HRID 1436664 reaction equation
N1C=C[CH:4]=[CH:3][CH:2]=1.[CH2:7]([O:9][C:10](=[O:26])[C:11]1[CH:23]=[C:22]([CH2:24][OH:25])[CH:21]=[C:13]([C:14]([N:16]([CH3:20])[CH2:17][CH2:18][CH3:19])=[O:15])[CH:12]=1)[CH3:8]>ClCCl>[CH2:7]([O:9][C:10](=[O:26])[C:11]1[CH:23]=[C:22]([CH2:24][O:25][CH:3]([CH3:4])[CH3:2])[CH:21]=[C:13]([C:14]([N:16]([CH3:20])[CH2:17][CH2:18][CH3:19])=[O:15])[CH:12]=1)[CH3:8]

Participants

4

Reactant 2

HCID 1049PyridineHCID 688164795-hydroxymethyl-N-methyl-N-propyl-isophthalamic acid ethyl ester

Product 1

HCID 68814924HCID 68814924, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Mix dichloromethane (1.8 mL), pyridine (56 μL, 0.7 mmol), and trifluomethanesulfonic anhydride (97 μL, 0.58 mmol) to a flask at −35 to −45° C. Add premixed 5-hydroxymethyl-N-methyl-N-propyl-isophthalamic acid ethyl ester (65 mg, 0.23 mmol) in dichloromethane (4 mL) dropwise at −40° C. Stir for 5 min and quench with isopropyl alcohol (2 mL). Dilute the reaction mixture with dichloromethane (10 mL), wash with water (2×10 mL), and concentrate to give the title compound and used directly in the next step without further purification.

Workup

  1. additionAdd
  2. customquench with isopropyl alcohol (2 mL)
  3. additionDilute the reaction mixture with dichloromethane (10 mL)
  4. washwash with water (2×10 mL)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-c249b9e6df04431ca8e4f7a4bdf1f687
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

Loading…