Pyridine → HCID 68814924, compound

HRID 732520Notes

Reaction equation

HRID 732520 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 mL, 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-e005bf004ffb4a639a06fd7573e34b81
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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