Potassium Carbonate → HCID 57961588, compound

HRID 541824Notes

Reaction equation

HRID 541824 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:15]=[CH:16][CH:17]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[Cl:26][C:27]1[N:32]=[C:31](Cl)[C:30]([Cl:34])=[CH:29][N:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:26][C:27]1[N:32]=[C:31]([NH:1][C:2]2[CH:3]=[C:4]([S:8]([NH:11][C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[CH:15]=[CH:16][CH:17]=3)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=2)[C:30]([Cl:34])=[CH:29][N:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 57962444HCID 57962444, compound

Product 1

HCID 57961588HCID 57961588, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl (3-{[(3-aminophenyl)sulfonyl]amino}phenyl)carbamate (0.30 g, 0.82 mmol) and 2,4,5-trichloropyrimidine (0.14 g, 0.75 mmol) in DMF (2 mL) was added potassium carbonate (0.12 g, 0.90 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 phase was extracted with EtOAc. The combined organics were washed with water and brine then dried (MgSO4), filtered, and concentrated. The resulted crude mixture was purified by column chromatography to give the desired product (70 mg, 18%). LCMS for C21H21Cl2N5O4S (M-tBu+H)+: m/z=454.0, 455.9. 1H NMR (500 MHz, DMSO-d6): δ 9.28 (s, 1H), 8.41 (s, 1H), 8.12 (br, 1H), 7.85 (dt, J=7.4, 1.8 Hz, 1H), 7.55 (br, 1H), 7.57 (dt, J=7.9, 1.8 Hz, 1H), 7.39 (s, 1H), 7.04 (m, 1H), 7.02 (dt, J=8.2, 2.0 Hz, 1H), 6.71 (dt, J=7.5, 1.8 Hz, 1H), 1.43 (s, 9H).

Workup

  1. customThe reaction was quenched with sat'd NH4Cl and water
  2. additionEtOAc was added
  3. customthe layers separated
  4. extractionThe aqueous phase 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 crude mixture
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-038451530cd1433f845ff59a87882b5e
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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