Pyridine → HCID 18368188, compound

HRID 379791Notes

Reaction equation

HRID 379791 reaction equation
[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH2:14])[CH:12]=2)[N:7](C(OCC)=O)[C:6]=1[C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl>[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:14][S:35]([CH3:34])(=[O:37])=[O:36])[CH:12]=2)[NH:7][C:6]=1[C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 18367823HCID 18367823, compound

Product 1

HCID 18368188HCID 18368188, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-acetylamino-5-amino-2-benzoyl-1-ethoxycarbonylindole (Example 99, step 1: 100 mg, 0.27 mmol) in dichloromethane (5 ml) and pyridine (33 μl, 0.41 mmol) was added methanesulfonyl chloride (25 μl, 0.32 mmol) and the mixture was stirred for 1 h. The mixture was partitioned between 2N aqueous HCl (30 ml) and ethyl acetate (30 ml), the organic layer separated and washed cocnsecutively with brine (10 ml), saturated aqueous sodium bicarbonate (10 ml), brine (10 ml) and dried (MgSO4). After removal of solvent the residue was diluted with ethanol (10 ml) and water (5 ml), and potassium hydroxide (0.5 g) added. The mixture was stirred for 4 h, poured into a saturated aqueous ammonium chloride (30 ml) and extracted with ethyl acetate (50 ml×2). The organic layer was washed with brine (50 ml), dried (MgSO4), and solvent removed by evaporation. The residue was recrystallized from methanol/dichloromethane/hexane to give 66 mg of the title compound as a yellow solid. m.p.: 260-261° C. 1H-NMR (DMSO-d6) δ: 11.7 (1H, br s), 9.63 (1H, s), 7.81-8.22 (2H, m), 7.40-7.64 (7H, m), 2.90 (3H, s), 164 (3H, s).

Workup

  1. customThe mixture was partitioned between 2N aqueous HCl (30 ml) and ethyl acetate (30 ml)
  2. customthe organic layer separated
  3. washwashed cocnsecutively with brine (10 ml), saturated aqueous sodium bicarbonate (10 ml), brine (10 ml)
  4. dry with materialdried (MgSO4)
  5. customAfter removal of solvent the residue
  6. additionwas diluted with ethanol (10 ml) and water (5 ml), and potassium hydroxide (0.5 g)
  7. additionadded
  8. stirringThe mixture was stirred for 4 h
  9. additionpoured into a saturated aqueous ammonium chloride (30 ml)
  10. extractionextracted with ethyl acetate (50 ml×2)
  11. washThe organic layer was washed with brine (50 ml)
  12. dry with materialdried (MgSO4), and solvent
  13. customremoved by evaporation
  14. customThe residue was recrystallized from methanol/dichloromethane/hexane

Sources & evidence

ORD record
ord-2038b9e0fbc64731ba3bdd7379e66027
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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