Dimethylformamide → HCID 9880863, compound

HRID 432606Notes

Reaction equation

HRID 432606 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3](C(O)=O)[CH2:2]1.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[CH:31]=[CH:32][C:27]([NH:26][C:42]([NH:40][CH:3]2[CH2:4][CH2:5][O:1][CH2:2]2)=[O:43])=[C:28]([OH:38])[C:29]=1[S:34](=[O:36])(=[O:35])[NH2:37]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 199401P,P-Diphenylphosphinic azideHCID 4661317(R)-Tetrahydro-3-furoic acidHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

Product 1

HCID 9880863HCID 9880863, compoundYield 5%

Conditions

Temperature
70 °C

Procedure

To a solution of Tetrahydro-furan-3-carboxylic acid (0.093 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 concentrated under reduced pressure. The crude residue was purified via HPLC to give 18 mg (5%) of N-[4-chloro-2-hydroxy-3-sulfamylphenyl]-N′-(3-tetrahydrofuryl)urea. 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. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified via HPLC

Sources & evidence

ORD record
ord-328012ee63144561832de4828a1c9ea2
Source dataset
uspto-grants-2003_12
Patent number
US06664259B2

Reaction notes

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