Imidazole → HCID 59203839, compound

HRID 2241826Notes

Reaction equation

HRID 2241826 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19].N1C=CN=C1>CN(C=O)C>[Si:22]([O:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH2:1])=[N:7][CH:6]=3)[O:9][C:10]=2[CH:16]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 795Imidazole2×HCID 28928tert-Butyldimethylsilyl chloride2×HCID 59203837HCID 59203837, compound

Product 1

HCID 59203839HCID 59203839, compoundYield 345.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(6-aminopyridin-3-yl)-1,3-benzoxazol-6-ol (0.95 mmol) in DMF (25 mL) was added tert-butylchlorodimethylsilane (1.05 mmol) and imidazole (2.38 mmol), the resulting mixture was stirred at room temperature for 3 hours. LCMS showed no conversion. Additional tert-butylchlorodimethylsilane (1.05 mmol) and imidazole (2.38 mmol) was added to the reaction mixture, then stirred at room temperature overnight. The reaction mixture was then partitioned between EtOAc (100 mL) and water (250 mL), and the aqueous layer was extracted twice with EtOAc (100 mL). The combined organic layers were washed with brine (100 mL), dried (Na2SO4), filtered and evaporated to give 1.121 g of a yellow solid. Purified by flash column chromatography (SiO2, Heptane:EtOAc 0→100%), to give the title compound (322.5 mg) as an ivory-white solid. 1H NMR δ ppm 8.67 (d, 1H) 8.01 (dd, 1H) 7.54 (d, 1H) 7.18 (d, 1H) 6.85 (dd, 1H) 6.77 (s, 2H) 6.57 (d, 1H) 0.97 (s, 9H) 0.22 (s, 6H); MS m/z 342 (M+H).

Workup

  1. stirringstirred at room temperature overnight
  2. customThe reaction mixture was then partitioned between EtOAc (100 mL) and water (250 mL)
  3. extractionthe aqueous layer was extracted twice with EtOAc (100 mL)
  4. washThe combined organic layers were washed with brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-82cbb8b74e4d47aaac274103cd853c43
Source dataset
uspto-grants-2010_03
Patent number
US07670591B2

Reaction notes

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