Potassium Carbonate → N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}-3-nitrobenzamide

HRID 541816Notes

Reaction equation

HRID 541816 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][NH:7][C:8](=[O:18])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1.[Cl:22][C:23]1[N:28]=[C:27](Cl)[C:26]([Cl:30])=[CH:25][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:22][C:23]1[N:28]=[C:27]([NH:2][C:3]2[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=2)[CH2:6][NH:7][C:8](=[O:18])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:26]([Cl:30])=[CH:25][N:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 66880486N-(3-Aminobenzyl)-3-nitrobenzamide Hydrochloride

Product 1

HCID 57961607N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}-3-nitrobenzamideYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3-aminobenzyl)-3-nitrobenzamide hydrochloride (0.70 g, 2.3 mmol) and 2,4,5-trichloropyrimidine (0.237 mL, 2.07 mmol) in DMF (5.5 mL) was added potassium carbonate (1.0 g, 7.2 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with sat'd NH4Cl and water. EtOAc was added and the layers separated. The aqueous layer was extracted with EtOAc twice. The combined organics were washed with water, dried, filtered and concentrated to give 1.25 grams of crude material, which was triturated with MeOH/EtOAc to give the desired product as an off-white powder (665 mg, 77%). LCMS for C18H13Cl2N5O3 (M+H)+: m/z=418.0, 420.0, 422.0. 1H NMR (400 MHz, DMSO-d6): δ 9.53 (s, 1H), 9.49 (t, J=2.0 Hz, 1H), 8.74 (t, J=2.0 Hz, 1H), 8.36 (m, 3H), 7.78 (t, J=8.0 Hz, 1H), 7.52 (s, 1H), 7.47 (d, J=8.0 Hz, 1H), 7.34 (t, J=7.6 Hz, 1H), 7.15 (d, J=8.0, 1H), 4.52 (d, J=6.0 Hz, 2H).

Workup

  1. customThe reaction was quenched with sat'd NH4Cl and water
  2. additionEtOAc was added
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with EtOAc twice
  5. washThe combined organics were washed with water
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give 1.25 grams of crude material, which
  10. customwas triturated with MeOH/EtOAc

Sources & evidence

ORD record
ord-a423db9f3da4457b80fa417074625599
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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