Triethylamine → HCID 69056237, compound

HRID 734640Notes

Reaction equation

HRID 734640 reaction equation
C(N(CC)CC)C.[CH:8]1([CH2:13][CH2:14][C:15](Cl)=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9]1.[NH2:18][C:19]1[NH:20][CH:21]=[C:22]([C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)[C:23]=1[C:24]([NH2:26])=[O:25]>O1CCCC1.O>[CH:8]1([CH2:13][CH2:14][C:15]([NH:18][C:19]2[NH:20][CH:21]=[C:22]([C:27]3[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=3)[C:23]=2[C:24]([NH2:26])=[O:25])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 660393-Cyclopentylpropionyl chlorideHCID 57845538HCID 57845538, compound

Product 1

HCID 69056237HCID 69056237, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.171 cm3 (1.22 mmol) of triethylamine and 0.098 mg (0.61 mmol) of 3-cyclopentylpropionyl chloride are added, at a temperature close to 25° C., to a solution of 0.15 g (0.61 mmol) of 2-amino-4-(4-nitrophenyl)-1H-pyrrole-3-carboxamide in 25 cm3 of tetrahydrofuran. After stirring for 16 hours at this temperature, the reaction medium is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is stirred in 40 cm3 of water and then extracted with three times 40 cm3 of ethyl acetate. The organic phase is washed with 80 cm3 of a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 0.218 g of 2-(3-cyclopentyl-propionylamino)-4-(4-nitrophenyl)-1H-pyrrole-3-carboxamide in the form of a green powder. 1H NMR (400 MHz, (CD3)2SO, —δ in ppm) 1.11 (m, 2H); from 1.42 to 1.65 (m, 6H); from 1.69 to 1.86 (m, 3H); 2.39 (t, J=8.0 Hz, 2H); from 6.17 to 8.50 (very broad m, 2H); 6.79 (d, J=2.5 Hz, 1H); 7.63 (d, J=9.0 Hz, 2H); 8.18 (d, J=9.0 Hz, 2H); 10.35 (broad s, 1H); 11.6 (broad s, 1H)

Workup

  1. concentrationthe reaction medium is concentrated to dryness under reduced pressure (2.7 kPa)
  2. customto give a residue which
  3. extractionextracted with three times 40 cm3 of ethyl acetate
  4. washThe organic phase is washed with 80 cm3 of a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-c3eb75b962764000bb4910641b58a440
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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