2-Nitrobenzoyl chloride → 3-(2-Nitro-benzoylamino)-furo[3,2-c]pyrazole-1,5-dicarboxylic acid 1-ethyl ester 5-propyl ester

HRID 1642333Notes

Reaction equation

HRID 1642333 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[O:14][C:13]2[C:12]([NH2:15])=[N:11][N:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:9]=2[CH:8]=1)=[O:6])[CH2:2][CH3:3].C(N(C(C)C)CC)(C)C.[N+:30]([C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35](Cl)=[O:36])([O-:32])=[O:31]>O1CCCC1>[CH2:1]([O:4][C:5]([C:7]1[O:14][C:13]2[C:12]([NH:15][C:35](=[O:36])[C:34]3[CH:38]=[CH:39][CH:40]=[CH:41][C:33]=3[N+:30]([O-:32])=[O:31])=[N:11][N:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:9]=2[CH:8]=1)=[O:6])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 118752-Nitrobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 426017253-Amino-furo[3,2-c]pyrazole-1,5-dicarboxylic acid 1-ethyl ester 5-propyl ester

Product 1

HCID 578786493-(2-Nitro-benzoylamino)-furo[3,2-c]pyrazole-1,5-dicarboxylic acid 1-ethyl ester 5-propyl esterYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-amino-furo[3,2-c]pyrazole-1,5-dicarboxylic acid 1-ethyl ester 5-propyl ester (500 mg, 1.606 mmol) and diisopropylethylamine (DIEA, 0.824 mL, 4.818 mmol) in tetrahydrofuran (THF, 20 mL) at 0° C., 2-nitro-benzoyl chloride (0.318 mL, 2.409 mmol) was added. The reaction mixture was kept at the same temperature for 10 minutes then allowed to reach room temperature and let react overnight. The solvent was removed under vacuum, the residue was dissolved in dichloromethane (DCM) and washed with a 10% solution of acetic acid (AcOH), water, saturated NaHCO3 and brine. The crude was purified on silica gel (eluant dichloromethane/methanol 96/4) yielding 512 mg (69%) of the title compound.

Workup

  1. customto reach room temperature
  2. customlet react overnight
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue was dissolved in dichloromethane (DCM)
  5. washwashed with a 10% solution of acetic acid (AcOH), water, saturated NaHCO3 and brine
  6. customThe crude was purified on silica gel (eluant dichloromethane/methanol 96/4)

Sources & evidence

ORD record
ord-f46b149c0e424338a2a73f391a7309dc
Source dataset
uspto-grants-2012_02
Patent number
US08119641B2

Reaction notes

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