Imidazole → HCID 57553390, compound

HRID 1698113Notes

Reaction equation

HRID 1698113 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[S: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.[CH3:18][C:19]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])[CH3:20].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)[S:9][C:10]=2[CH:16]=1)([C:19]([CH3:21])([CH3:20])[CH3:18])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 24804233HCID 24804233, compound

Product 1

HCID 57553390HCID 57553390, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(6-aminopyridin-3-yl)-1,3-benzothiazol-6-ol (177 mg, 0.73 mmol), TBDMSCl (121 mg, 1.1 equiv) and imidazole (124 mg, 2.5 equiv) in DMF (2.0 ml) was stirred at ambient temperature for 2 h. The reaction mixture was then partitioned between water and ethyl acetate. The aqueous phase was extracted twice with ethyl acetate and the combined organics dried (MgSO4) and concentrated in vacuo. The crude product thus obtained was purified by silica gel chromatography, using a mixture of DCM and methanol (95:5) as eluent, to yield 200 mg of the title compound as a white solid. 1H NMR δ 8.56 (d, 1H) 7.96 (dd, 1H) 7.80 (d, 1H) 7.54 (d, 1H) 6.98 (dd, 1H) 6.67 (s, 2H) 6.56 (d, 1H) 0.97 (s, 9H) 0.22 (s, 6H); MS m/z (M+H) 358.

Workup

  1. customThe reaction mixture was then partitioned between water and ethyl acetate
  2. extractionThe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialthe combined organics dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product thus obtained
  6. customwas purified by silica gel chromatography
  7. additiona mixture of DCM and methanol (95:5) as eluent

Sources & evidence

ORD record
ord-0180537df22f4cee8a0a06818972a8fa
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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