Imidazole → HCID 86691458, compound

HRID 1618861Notes

Reaction equation

HRID 1618861 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH:11]([CH3:13])[N:10]([CH3:14])[C:9]2=[O:15])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.[C:27]([Si:31](Cl)([CH3:33])[CH3:32])([CH3:30])([CH3:29])[CH3:28]>ClCCl>[Si:31]([O:1][C:2]1[CH:3]=[C:4]([C:8]2([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:12][CH:11]([CH3:13])[N:10]([CH3:14])[C:9]2=[O:15])[CH:5]=[CH:6][CH:7]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86691459HCID 86691459, compound

Product 1

HCID 86691458HCID 86691458, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Product of Step 6 (4.9 g) was dissolved in dichloromethane (200 mL). To this, imidazole (5 g) and tertiarybutyldimethylsilyl chloride (5 g) was added. The reaction mixture was stirred at 25° C. for 16 hrs. Then, the reaction mixture was extracted with water (200 mL) and the organic layer was dried on anhydrous magnesium sulfate. The organic layer was filtered and concentrated under vacuum. The crude product was loaded on a SNAP cartridge containing 340 g silica gel and eluted with a gradient of ethyl acetate and hexane using the BIOTAGE® AB ISOLERA™ flash chromatography system. Fractions containing product were pooled and evaporated to obtain product of Step 7 as a viscous, colorless oil. Yield of purified product: 2.75 g. 1H NMR (CDCl3): 0.1 δ (6H, —Si—(CH3)2), 0.9 δ (9H, (—CH3)3 of tertiary butyl), 1.3 δ (3H, —CH—CH3 of isopropyl), 2.8 δ (3H, —N—(CH3)), 2.25, 3.1, 3.5 δ (1H, 1H, 1H —CH2-CH—CH3 of isopropyl), 6.8-7.5 δ (9H, phenyl rings). Mass spectrometry: m/z=396 (M+H).

Workup

  1. extractionThen, the reaction mixture was extracted with water (200 mL)
  2. dry with materialthe organic layer was dried on anhydrous magnesium sulfate
  3. filtrationThe organic layer was filtered
  4. concentrationconcentrated under vacuum
  5. additioncontaining 340 g silica gel
  6. washeluted with a gradient of ethyl acetate and hexane using the BIOTAGE® AB ISOLERA™ flash chromatography system
  7. additionFractions containing product
  8. customevaporated

Sources & evidence

ORD record
ord-39d2491b17db45578e59221f9db20124
Source dataset
uspto-grants-2014_07
Patent number
US08771964B2

Reaction notes

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