Hydrochloric Acid → HCID 53309969, compound

HRID 1987116Notes

Reaction equation

HRID 1987116 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]M+, 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-00fe167446d94a5f8d063c7c1b2b581a
Source dataset
uspto-grants-2009_06
Patent number
US07550478B2

Reaction notes

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