Water → HCID 178522814, compound

HRID 714335Notes

Reaction equation

HRID 714335 reaction equation
[C:1]([NH:9][C:10]1[CH:11]=[C:12]([CH:23]=[C:24]([O:26]C)[N:25]=1)[C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[Na+].Cl[Si](C)(C)C.O>C(#N)C>[C:1]([NH:9][C:10]1[CH:11]=[C:12]([CH:23]=[C:24]([OH:26])[N:25]=1)[C:13]([NH:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 671538302-benzamido-N-benzyl-6-methoxyisonicotinamide

Product 1

HCID 178522814HCID 178522814, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-benzamido-N-benzyl-6-methoxyisonicotinamide (0.18 g, 0.50 mmol) and sodium iodide (0.45 g, 3.00 mmol) in acetonitrile (10 mL) was added chlorotrimethylsilane (0.39 mL, 3.00 mmol) and water (0.1 mL) at 0° C. The resulting solution was stirred at ambient temperature for 20 hours, quenched with methanol (10 mL), stirred for 10 minutes and concentrated in vacuo. The residue was washed with saturated sodium bicarbonate solution (5 mL) and water (5 mL). The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to a minimum volume and triturated with ethyl acetate. The solid was filtered and dried in vacuo to give 2-benzamido-N-benzyl-6-hydroxyisonicotinamide as a colorless solid (0.04 g, 20%): mp 257° C. (dec); 1H NMR (300 MHz, DMSO-d6) δ 11.07 (br s, 1H), 9.20 (br s, 1H), 8.46-6.59 (m, 12H), 4.37 (br s, 2H); MS (ES+) m/z 348.5 (M+1).

Workup

  1. customquenched with methanol (10 mL)
  2. stirringstirred for 10 minutes
  3. concentrationconcentrated in vacuo
  4. washThe residue was washed with saturated sodium bicarbonate solution (5 mL) and water (5 mL)
  5. dry with materialThe organic solution was dried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a minimum volume
  8. customtriturated with ethyl acetate
  9. filtrationThe solid was filtered
  10. customdried in vacuo

Sources & evidence

ORD record
ord-d0f589832be449f2bc6b6695caa7a7d0
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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