Acetic Acid → HCID 58467837, compound

HRID 1614935Notes

Reaction equation

HRID 1614935 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=3)(=[O:19])=[O:18])[CH:13]=[CH:14][CH:15]=2)[C:5]([Cl:29])=[CH:4][N:3]=1.CO.C(O)(=O)C.C([O-])(O)=O.[Na+]>[Fe].CCOC(C)=O.O>[NH2:26][C:22]1[CH:21]=[C:20]([S:17]([NH:16][C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][NH:8][C:6]3[C:5]([Cl:29])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH:11]=2)(=[O:18])=[O:19])[CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 58467921HCID 58467921, compound

Product 1

HCID 58467837HCID 58467837, compoundYield 25%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Into a reaction flask was added N-(3-{[(2,5-dichloropyrimidin-4-yl)amino]methyl}phenyl)-3-nitrobenzenesulfonamide (0.20 g, 0.44 mmol), methanol (20 mL), acetic acid (2.0 mL), and water (1 mL). Then iron (0.25 g, 4.5 mmol) powder was added. The reaction mixture was heated at 70° C. for 2 hours. After cooling, the mixture was filtered and washed with EtOAc. The filtrate was concentrated under vacuum to give a residue, which was treated with NaHCO3 (saturated aqueous solution) and EtOAc. The organic layer was dried and concentrated under vacuum. The resulting crude product was then purified by silica gel column chromatography to provide the desired product (46 mg, 25%). LCMS for C17H16Cl2N5O2S (M+H)+: m/z=424.0, 426.0.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. washwashed with EtOAc
  4. concentrationThe filtrate was concentrated under vacuum
  5. customto give a residue, which
  6. customThe organic layer was dried
  7. concentrationconcentrated under vacuum
  8. customThe resulting crude product was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1108f90391f24727a52c952f550e6108
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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