Dimethylformamide → HCID 9902927, compound

HRID 432608Notes

Reaction equation

HRID 432608 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11](C(O)=O)[CH2:10][CH2:9]1)=O)(C)(C)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[NH2:34][C:35]1[C:36]([OH:46])=[C:37]([S:42]([NH2:45])(=[O:44])=[O:43])[C:38]([Cl:41])=[CH:39][CH:40]=1.C[N:48]([CH:50]=[O:51])C>>[Cl:41][C:38]1[C:37]([S:42]([NH2:45])(=[O:44])=[O:43])=[C:36]([OH:46])[C:35]([NH:34][C:50]([NH:48][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:51])=[CH:40][CH:39]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 199401P,P-Diphenylphosphinic azideHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

Product 1

HCID 9902927HCID 9902927, compound

Conditions

Temperature
80 °C

Procedure

To a solution of piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (0.23 g, 1.0 mmol) in DMF (0.5 mL) was added DPPA (0.215 mL, 1.0 mmol) and TEA (0.139 mL, 1.0 mmol) and the reaction heated at 80° C. After 18 hrs, 3-Amino-6-chloro-2-hydroxy-benzenesulfonamide (1.0 mmol) was added and the reaction heated at 80° 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 12 mg of 6-Chloro-2-hydroxy-3-(3-piperidin-4-yl-ureido)-benzenesulfonamide. LC-MS (m/z) 349 (M+).

Workup

  1. temperaturethe reaction heated at 80° 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-248dca54855e483682b1af55e939b6ce
Source dataset
uspto-grants-2003_12
Patent number
US06664259B2

Reaction notes

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