Methyl iodide → HCID 86659294, compound

HRID 335148Notes

Reaction equation

HRID 335148 reaction equation
[ClH:1].Cl.[CH3:3][C:4]1[N:5]=[C:6]([NH:9][C:10]2[N:15]=[CH:14][C:13]([S:16][CH2:17][C:18]3[C:23]([OH:24])=[CH:22][CH:21]=[CH:20][N:19]=3)=[CH:12][C:11]=2[O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[S:7][CH:8]=1.[H-].[Na+].[CH3:34]I>CN(C=O)C>[ClH:1].[CH3:34][O:24][C:23]1[C:18]([CH2:17][S:16][C:13]2[CH:12]=[C:11]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:10]([NH:9][C:6]3[S:7][CH:8]=[C:4]([CH3:3])[N:5]=3)=[N:15][CH:14]=2)=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 24764892HCID 24764892, compound

Product 1

HCID 86659294HCID 86659294, compoundYield 4.22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Placed 2-((6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)methyl)pyridine-3-ol (prepared in Example 69) (0.180 g, 0.426 mmol) in DMF (5 mL) and cooled to 0° C. Sodium hydride (0.0307 g, 1.28 mmol) was added and stirred for 10 minutes then MeI (0.0605 g, 0.426 mmol) was added stirred at ambient temperature for 30 minutes. Added water and extracted with CH2Cl2. The organic layer was concentrated and purified by silica gel. The product was still impure. Mixture was purified by medium pressure reverse phase followed by two high pressure reverse phase purifications. Combined all clean fractions' then dissolved in CH2Cl2 and added HCl in ether, then concentrated to give the title compound (0.0085 g, 4.22% yield). 1H NMR (d6-DMSO) δ 8.14 (m, 1H), 8.10 (d, 1H), 7.65 (m, 1H), 7.55 (m, 1H), 7.34-7.27 (m, 3H), 7.03 (m, 1H), 6.85 (d, 2H), 6.36 (s, 1H), 4.24 (s, 2H), 3.17 (s, 3H), 2.18 (s, 3H).

Workup

  1. stirringstirred at ambient temperature for 30 minutes
  2. extractionAdded water and extracted with CH2Cl2
  3. concentrationThe organic layer was concentrated
  4. custompurified by silica gel
  5. customMixture was purified by medium pressure
  6. dissolutionthen dissolved in CH2Cl2
  7. additionadded HCl in ether
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-20af58e0aee64f26ba1b74f0477a6f6d
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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