Benzenesulfonamide → HCID 86752960, compound

HRID 481423Notes

Reaction equation

HRID 481423 reaction equation
[CH:1]1([C:4]2[N:14]([CH2:15][C:16]3[S:20][C:19]([C:21]4([C:26]([OH:28])=[O:27])[CH2:25][CH:24]=[CH:23][CH2:22]4)=[CH:18][CH:17]=3)[C:7]3=[N:8][C:9]([CH3:13])=[CH:10][C:11]([CH3:12])=[C:6]3[N:5]=2)[CH2:3][CH2:2]1.[C:29]1([S:35]([NH2:38])(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[C:29]1([S:35]([NH2:38])(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[CH:1]1([C:4]2[N:14]([CH2:15][C:16]3[S:20][C:19]([C:21]4([C:26]([OH:28])=[O:27])[CH2:25][CH:24]=[C:23]=[CH:22]4)=[CH:18][CH:17]=3)[C:7]3=[N:8][C:9]([CH3:13])=[CH:10][C:11]([CH3:12])=[C:6]3[N:5]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 7370BenzenesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 9952487HCID 9952487, compound

Product 1

HCID 86752960HCID 86752960, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

A mixture of 1-[5-(2-cyclopropyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)thiophen-2-yl]cyclopenten-3-ene carboxylic acid (Example 3) (500 mg, 1.27 mmol) and 1,1-carbonyl diimidazole (250 mg, 1.27 mmol) in THF (25 ml) was heated under reflux for 3 hours, then a solution of benzenesulfonamide (242 mg, 1.6 mmol) and DBU (243 mg, 1.6 mmol) in THF (2.0 ml) was added. The reaction mixture was heated at 40° C. for 19 hours, cooled to 23° C. and concentrated in vacuo. The residue was dissolved in water and acidified with 10% aqueous NaH2PO3. The aqueous mixture was extracted with EtOAc (3×25 ml). The combined extracts were dried and concentrated in vacuo. The crude residue was chromatographed on SiO2 gel using 2% MeOH/EtOAc to give 406 mg of the title compound (60% yield).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperaturecooled to 23° C.
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in water
  6. extractionThe aqueous mixture was extracted with EtOAc (3×25 ml)
  7. customThe combined extracts were dried
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was chromatographed on SiO2 gel

Sources & evidence

ORD record
ord-9c982d0cc54a4606a3ea9fa6b0b8adf8
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Reaction notes

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