Methanol → 3-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide

HRID 548722Notes

Reaction equation

HRID 548722 reaction equation
I[Si](C)(C)C.[OH:6][C:7]1[CH:8]=[C:9]([CH:20]=[C:21]([O:23][C@@H:24]([CH3:28])[CH2:25][O:26]C)[CH:22]=1)[C:10]([NH:12][C:13]1[CH:18]=[N:17][C:16]([CH3:19])=[CH:15][N:14]=1)=[O:11].CO.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[OH:6][C:7]1[CH:8]=[C:9]([CH:20]=[C:21]([O:23][C@@H:24]([CH3:28])[CH2:25][OH:26])[CH:22]=1)[C:10]([NH:12][C:13]1[CH:18]=[N:17][C:16]([CH3:19])=[CH:15][N:14]=1)=[O:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 59127168(S)-3-hydroxy-5-(1-methoxypropan-2-yloxy)-N-(5-methylpyrazin-2-yl)benzamide

Product 1

HCID 591271143-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamideYield 84.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Iodotrimethylsilane (5.61 mL, 39.39 mmol) was added to 3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide (2.5 g, 7.88 mmol) in acetonitrile (25 mL) and the reaction stirred at RT for 20 hours. Methanol (15 mL) was added and stirred for 1 hour then a saturated solution of sodium thiosulphate (10 mL) was added and stirred for a further 20 mins. The volatiles were removed in vacuo and the aqueous residue extracted into ethyl acetate (2×150 mL). The organics were washed with water (100 mL), brine (100 mL), dried (MgSO4), and reduced in vacuo to give the desired compound as a white solid (2.03 g). 1H NMR δ (d6-DMSO): 1.22 (d, 3H), 2.48 (s, 3H), 3.44-3.59 (m, 2H), 4.50 (sextet, 1H), 4.87 (t, 1H), 6.53 (t, 1H), 6.98 (s, 1H), 7.11 (s, 1H), 8.36 (s, 1H), 9.25 (s, 1H), 9.75 (s, 1H), 10.89 (s, 1H); m/z 304 (M+H)+

Workup

  1. stirringstirred for 1 hour
  2. stirringstirred for a further 20 mins
  3. customThe volatiles were removed in vacuo
  4. extractionthe aqueous residue extracted into ethyl acetate (2×150 mL)
  5. washThe organics were washed with water (100 mL), brine (100 mL)
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-06da347637e247629d3b7dffdb45a94f
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

Loading…