Acetyl chloride → HCID 57845576, compound

HRID 734643Notes

Reaction equation

HRID 734643 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[NH2:12][C:13]1[NH:14][CH:15]=[C:16]([C:21]2[CH:22]=[N:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)[C:17]=1[C:18]([NH2:20])=[O:19]>O1CCCC1.C(OCC)(=O)C>[C:8]([NH:12][C:13]1[NH:14][CH:15]=[C:16]([C:21]2[CH:22]=[N:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)[C:17]=1[C:18]([NH2:20])=[O:19])(=[O:10])[CH3:9]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 578455532-amino-4-(6-nitropyridin-3-yl)-1H-pyrrole-3-carboxamide

Product 1

HCID 57845576HCID 57845576, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.226 cm3 (1.62 mmol) of triethylamine and 0.058 cm3 (0.809 mmol) of acetyl chloride are added, at a temperature close to 20° C. under an argon atmosphere, to a solution of 0.20 g (0.809 mmol) of 2-amino-4-(6-nitropyridin-3-yl)-1H-pyrrole-3-carboxamide in 40 cm3 of tetrahydrofuran. After stirring for 3 hours at this temperature, the reaction medium is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is diluted in 200 cm3 of ethyl acetate and then washed with 50 cm3 of water and 50 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 0.15 g of 2-acetylamino-4-(6-nitropyridin-3-yl)-1H-pyrrole-3-carboxamide in the form of a green powder. 1H NMR (400 MHz, (CD3)2SO, —δ in ppm) 2.11 (s, 3H); 6.90 (broad m, 2H); 6.95 (d, J=3.0 Hz, 1H); 8.13 (dd, J=2.5 and 8.5 Hz, 1H); 8.27 (d, J=8.5 Hz, 1H); 8.65 (d, J=2.5 Hz, 1H); 10.2 (s, 1H); 11.7 (broad m, 1H).

Workup

  1. concentrationthe reaction medium is concentrated to dryness under reduced pressure (2.7 kPa)
  2. customto give a residue which
  3. washwashed with 50 cm3 of water and 50 cm3 of a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-16b6c2cbb4d34232953901c51f6b2354
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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