Triethylamine → N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]phenyl}-2-(3-nitrophenyl)acetamide

HRID 541833Notes

Reaction equation

HRID 541833 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:20])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[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+].C(N(CC)CC)C>CN(C=O)C>[Cl:22][C:23]1[N:28]=[C:27]([NH:1][C:2]2[CH:3]=[C:4]([NH:8][C:9](=[O:20])[CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=3)[CH:5]=[CH:6][CH:7]=2)[C:26]([Cl:30])=[CH:25][N:24]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 66881204N-(3-Aminophenyl)-2-(3-nitrophenyl)acetamide Hydrochloride

Product 1

HCID 57962398N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]phenyl}-2-(3-nitrophenyl)acetamideYield 54.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3-aminophenyl)-2-(3-nitrophenyl)acetamide-hydrogen chloride (0.11 g, 0.35 mmol) and 2,4,5-trichloropyrimidine (0.065 g, 0.35 mmol) in DMF (1 mL) was added potassium carbonate (0.20 g, 1.4 mmol). The resulting mixture was stirred overnight at room temperature. Additional triethylamine (0.099 mL, 0.71 mmol) was then added an stirred overnight again. The reaction was quenched with sat'd NH4Cl and water. EtOAc was added and the layers separated. The aqueous was extracted with EtOAc. The combined organics were washed with water and brine then dried (MgSO4), filtered, and concentrated. The resulted mixture was purified by column chromatography to give the desired product (0.080 g, 53%). LCMS for C18H13Cl2N5O3 (M+H)+: m/z=418.0, 419.9. 1H NMR (400 MHz, DMSO-d6): δ 10.33 (s, 1H), 9.53 (s, 1H), 8.35 (s, 1H), 8.23 (t, J=2.0 Hz, 1H), 8.12 (ddd, J=8.2, 2.4, 1.0 Hz, 1H), 7.82 (t, J=2.0 Hz, 1H), 7.78 (dt, J=7.8, 1.4 Hz, 1H), 7.62 (t, J=7.9 Hz, 1H), 7.36 (dt, J=8.0, 1.7 Hz, 1H), 7.30 (t, J=7.8 Hz, 1H), 7.25 (dt, J=8.0, 1.7 Hz, 1H).

Workup

  1. customThe reaction was quenched with sat'd NH4Cl and water
  2. additionEtOAc was added
  3. customthe layers separated
  4. extractionThe aqueous was extracted with EtOAc
  5. washThe combined organics were washed with water and brine
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulted mixture was purified by column chromatography

Sources & evidence

ORD record
ord-37849553a50f47a387c6b238ef58291b
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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