4-Nitrobenzoic Acid → HCID 17615467, compound

HRID 1787706Notes

Reaction equation

HRID 1787706 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7](C(O)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.CN([C:25]([O:29]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(N(CC)CC)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:11][CH:12]=1)[C:25]([NH:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:29])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 316701-PyrrolidinepropanamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 17615467HCID 17615467, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

500 mg of 4-nitrobenzoic acid is dissolved in 20 ml of dimethylformamide, mixed with 370 μl of triethylamine, 342 mg of N-(3-aminopropyl)-pyrrolidine and 866 mg TBTU, and stirred for 20 hours at room temperature. The reaction mixture is mixed with semi-saturated sodium bicarbonate solution and extracted with dichloromethane. The organic solution is washed with saturated sodium chloride solution, dried on sodium sulfate, concentrated by evaporation, and after purification by chromatography on silica gel, 502 mg of the title compound is obtained.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic solution is washed with saturated sodium chloride solution
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customafter purification by chromatography on silica gel

Sources & evidence

ORD record
ord-a93efac43ae64714959bf862a476e87d
Source dataset
uspto-grants-2009_03
Patent number
US07511059B2

Reaction notes

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