Hydrochloric Acid → HCID 53309969, compound

HRID 222289Notes

Reaction equation

HRID 222289 reaction equation
[O:1]=[C:2]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11]=2)[CH:6]=[CH:5][C:4]2[CH:19]=[CH:20][C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][C:3]1=2.[BH4-].[Na+].Cl>CO>[OH:1][CH:2]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:11]=2)[CH:6]=[CH:5][C:4]2[CH:19]=[CH:20][C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][C:3]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 15981007HCID 15981007, compound

Product 1

HCID 53309969HCID 53309969, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred slurry of N-(5-oxo-3-phenyl-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl)methanesulfonamide (0.50 g, 1.3 mmol) in MeOH (30 mL) was added NaBH4 (100 mg, 2.6 mmol). The reaction mixture was left to stir for 30 min, treated with 1 N HCl and then 1 N NaOH, and concentrated. The residue was diluted with EtOAc and washed with brine. The organic layer was dried (Na2SO4), concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CD3OD) δ 8.66 (d, 1H); 8.38 (d, 1H); 7.15-7.71 (m, 10H); 5.28 (s, 1H); 2.96 (s, 3H). LRMS (APCI) calc'd for (C21H19N2O3S) [M+H]+, 379.1; found 379.1.

Workup

  1. waitThe reaction mixture was left
  2. concentration1 N NaOH, and concentrated
  3. additionThe residue was diluted with EtOAc
  4. washwashed with brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-b5503794bc4b4ccb8963ca707cb48c3d
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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