Imidazole → HCID 69556712, compound

HRID 1168321Notes

Reaction equation

HRID 1168321 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]2)=[N:9][CH:10]=1)=[O:4].[C:18]([Si:22]([CH3:25])([CH3:24])Cl)([CH3:21])([CH3:20])[CH3:19].N1C=CN=C1>CN(C)C=O>[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([O:17][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:25])[CH3:24])[CH2:13][CH2:12]2)=[N:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 69556362HCID 69556362, compound

Product 1

HCID 69556712HCID 69556712, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.1 g (42.9 mmol) 4-hydroxy-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid methylamide, 8.0 g (52 mmol) tert-butyldimethylchlorosilane and 6.5 g (94 mmol) imidazole in 90 ml N,N-dimethylformamide was stirred at room temperature over night. The reaction was quenched with water. The resulting suspension was extracted with ethyl acetate. The organic extract was washed with 3 portions of water. The combined aqueous layers were extracted with 3 portions of dichloromethane. The combined organic extracts were dried with sodium sulfate, concentrated and dried in vacuo (0.5 mbar) at 80° C. Flash column chromatography afforded 14.6 g (97.3%) of the title compound as a light yellow solid. MS m/e (%): 349 (M+, 21).

Workup

  1. customThe reaction was quenched with water
  2. extractionThe resulting suspension was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with 3 portions of water
  5. extractionThe combined aqueous layers were extracted with 3 portions of dichloromethane
  6. dry with materialThe combined organic extracts were dried with sodium sulfate
  7. concentrationconcentrated
  8. customdried in vacuo (0.5 mbar) at 80° C

Sources & evidence

ORD record
ord-3d9522b9d0e2451ea9b577ccfc59d3e1
Source dataset
uspto-grants-2003_09
Patent number
US06624176B2

Reaction notes

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