Triethylamine → Pyridine-3,4-dicarboxylic acid bis-[(4-phenyl-butyl)-amide]

HRID 1454128Notes

Reaction equation

HRID 1454128 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[C:3]([C:10]([OH:12])=O)[CH:2]=1.O.ON1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2N=N1.[C:24]1([CH2:30][CH2:31][CH2:32][CH2:33][NH2:34])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([N:37]([CH2:40][CH3:41])CC)C.Cl.CN(C)[CH2:45][CH2:46]CN=C=NCC>CN(C=O)C>[C:18]1([CH2:45][CH2:46][CH2:41][CH2:40][NH:37][C:10]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][C:4]=2[C:7]([NH:34][CH2:33][CH2:32][CH2:31][CH2:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:9])=[O:12])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10273Cinchomeronic acidHCID 83242BenzenebutanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 18727498Pyridine-3,4-dicarboxylic acid bis-[(4-phenyl-butyl)-amide]Yield 102.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,4-Pyridinedicarboxylic acid (1 g; 6.0 mmol) is slurried in DMF (50 mL) at ambient temperature. To this reaction mixture is added sequentially 1-hydroxybenzotriazole hydrate (2.43 g; 18.0 mmol), 4-phenylbutylamine (2.08 mL; 13.2 mmol), triethylamine (1.67 mL; 12.0 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (2.87 g; 15.0 mmol). The reaction mixture is stirred for 18 hours at ambient temperature. The batch is poured onto ethyl acetate (300 mL), then extracted sequentially with water (100 mL), 1N HCl (100 mL), saturated aqueous sodium bicarbonate (50 mL), and brine (50 mL). The organic phase is dried over MgSO4, filtered, and concentrated in vacuo affording the desired product (2.65 g) as a semi-solid. ESMS: MH+ 430.0.

Workup

  1. additionThe batch is poured onto ethyl acetate (300 mL)
  2. extractionextracted sequentially with water (100 mL), 1N HCl (100 mL), saturated aqueous sodium bicarbonate (50 mL), and brine (50 mL)
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-444ef3a4d4a34159ba514961f4fdf438
Source dataset
uspto-grants-2009_01
Patent number
US07476680B2

Reaction notes

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