Triethylamine → Methyl 6-[(3-{[(benzyloxy)carbonyl](methyl)amino}propyl)(methyl)carbamoyl]pyridine-3-carboxylate

HRID 446504Notes

Reaction equation

HRID 446504 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1)=[O:4].[CH2:14]([N:16](CC)CC)C.C(Cl)(=O)C(C)(C)C.CN[CH:30]([NH:33][CH3:34])[CH2:31][CH3:32].[CH2:35]([O:42][C:43](Cl)=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl>[CH2:35]([O:42][C:43]([N:16]([CH3:14])[CH2:32][CH2:31][CH2:30][N:33]([CH3:34])[C:11]([C:8]1[N:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1)=[O:13])=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 5

HCID 8471Triethylamine2×HCID 10387Benzyl chloroformateHCID 62493Pivaloyl chlorideHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 22287041HCID 22287041, compound

Product 1

HCID 66671574Methyl 6-[(3-{[(benzyloxy)carbonyl](methyl)amino}propyl)(methyl)carbamoyl]pyridine-3-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-(Methoxycarbonyl)pyridine-2-carboxylic acid (700 mg, 3.86 mmol) was dissolved in methylene chloride (40 mL), triethylamine (0.805 mL, 5.79 mmol) and pivaloyl chloride (0.524 mL, 4.25 mmol) were added under ice cooling, and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was added dropwise to a solution of N,N′-dimethylpropanediamine (1.18 g, 11.6 mmol) in methylene chloride (40 mL) under ice cooling, and the mixture was stirred overnight at room temperature. Triethylamine (4.03 mL, 29.0 mmol) and benzyloxycarbonyl chloride (4.14 mL, 29.0 mmol) were added under ice cooling, and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:3→0:100, v/v) to give the title compound (1.23 g; yield, 80%) as a colorless oily substance.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-b5c48cd6865443eebb047be2d85aa929
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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