Dimethylformamide → HCID 10110162, compound

HRID 432610Notes

Reaction equation

HRID 432610 reaction equation
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5](C(O)=O)[CH2:4]1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[NH2:29][C:30]1[C:31]([OH:41])=[C:32]([S:37]([NH2:40])(=[O:39])=[O:38])[C:33]([Cl:36])=[CH:34][CH:35]=1.C[N:43]([CH:45]=[O:46])C>>[Cl:36][C:33]1[C:32]([S:37]([NH2:40])(=[O:39])=[O:38])=[C:31]([OH:41])[C:30]([NH:29][C:45]([NH:43][CH:5]2[CH2:6][CH2:7][CH2:8][CH:3]([O:2][CH3:1])[CH2:4]2)=[O:46])=[CH:35][CH:34]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 199401P,P-Diphenylphosphinic azideHCID 37022803-methoxycyclohexanecarboxylic acidHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

Product 1

HCID 10110162HCID 10110162, compound

Conditions

Temperature
70 °C

Procedure

To a solution of 3-Methoxy-cyclohexanecarboxylic acid (0.143 mL) in DMF (0.5 mL) was added DPPA (0.25 mL ) and TEA (0.25 mL) and the reaction heated at 70° C. After 18 hrs, 3-Amino-6-chloro-2-hydroxy-benzenesulfonamide (0.222 g) 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 3 mg of 6-Chloro-2-hydroxy-3-[3-(3-methoxy-cyclohexyl)-ureido]-benzenesulfonamide. LC-MS (m/z) 378 (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-55ff25b5f317400790f4c654c4073286
Source dataset
uspto-grants-2003_12
Patent number
US06664259B2

Reaction notes

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