Dimethylformamide → HCID 9923824, compound

HRID 1884901Notes

Reaction equation

HRID 1884901 reaction equation
[CH2:1]([CH:3]([CH2:7][CH3:8])C(O)=O)[CH3:2].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[NH2:26][C:27]1[C:28]([OH:38])=[C:29]([S:34]([NH2:37])(=[O:36])=[O:35])[C:30]([Cl:33])=[CH:31][CH:32]=1.C[N:40]([CH:42]=[O:43])C>>[Cl:33][C:30]1[C:29]([S:34]([NH2:37])(=[O:36])=[O:35])=[C:28]([OH:38])[C:27]([NH:26][C:42]([NH:40][CH:3]([CH2:1][CH3:2])[CH2:7][CH3:8])=[O:43])=[CH:32][CH:31]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 69152-Ethylbutyric acidHCID 199401P,P-Diphenylphosphinic azideHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

Product 1

HCID 9923824HCID 9923824, compoundYield 15%

Conditions

Temperature
70 °C

Procedure

To a solution of 2-ethylbutyric acid (0.125 mL, 1.0 mmol) in DMF (0.5 mL) was added DPPA (0.25 mL, 1.2 mmol) and TEA (0.25 mL, 1.8 mmol) and the reaction heated at 70° C. After 18 hrs, 3-Amino-6-chloro-2-hydroxy-benzenesulfonamide (1.0 mmol) was added and the reaction heated at 70° C. After 18 hrs, the reaction mixture was quenched with water and extracted with ethyl acetate. The organic layers were dried over anhydrous magnesium sulfate, and concentraed under reduced pressure. The crude residue was purified via HPLC to give 51 mg (15%) of 6-Chloro-3-[3-(1-ethyl-propyl)-ureido]-2-hydroxy-benzenesulfonamide. LC-MS (m/z) 336 (M+).

Workup

  1. temperaturethe reaction heated at 70° C
  2. waitAfter 18 hrs
  3. customthe reaction mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  6. customThe crude residue was purified via HPLC

Sources & evidence

ORD record
ord-d45fdd45130c4a92ae8f694637ce609c
Source dataset
uspto-grants-2004_07
Patent number
US06767922B2

Reaction notes

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