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

HRID 541808Notes

Reaction equation

HRID 541808 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[CH2:6][NH:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)(=[O:10])=[O:9].[Cl:23][C:24]1[N:29]=[C:28](Cl)[C:27]([Cl:31])=[CH:26][N:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:23][C:24]1[N:29]=[C:28]([NH:2][C:3]2[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=2)[CH2:6][NH:7][S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)(=[O:9])=[O:10])[C:27]([Cl:31])=[CH:26][N:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 66880208N-(3-Aminobenzyl)-3-nitrobenzenesulfonamide Hydrochloride

Product 1

HCID 57961735N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]benzyl}-3-nitrobenzenesulfonamideYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3-aminobenzyl)-3-nitrobenzenesulfonamide hydrochloride (0.400 g, 1.16 mmol) and 2,4,5-trichloropyrimidine (0.12 mL, 1.06 mmol) in DMF (2.8 mL) was added potassium carbonate (0.51 g, 3.7 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with saturated (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 660 mg of crude residue, which was purified by Combi-Flash column chromatography (12 g column, 0 to 30% EtOAc in hexane) to give the desired product (135 mg, 28%). LCMS for C17H13Cl2N5O4S (M+H)+: m/z=453.9, 455.9, 457.9. 1H NMR (400 MHz, CD3OD): δ 8.85 (s, 1H), 8.48 (t, J=2.0 Hz, 1H), 8.29 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 8.21 (s, 1H), 8.08 (ddd, J=8.0, 1.6, 0.8 Hz, 1H), 7.64 (t, J=8.0 Hz, 1H), 7.41 (m, 2H), 7.17 (t, J=8.0 Hz, 1H), 4.21 (s, 2H).

Workup

  1. customThe reaction was quenched with saturated (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 660 mg of crude residue, which
  10. customwas purified by Combi-Flash column chromatography (12 g column, 0 to 30% EtOAc in hexane)

Sources & evidence

ORD record
ord-13cbae393bd24d12848da69b225824ca
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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