Imidazole → HCID 68495874, compound

HRID 1944204Notes

Reaction equation

HRID 1944204 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][C:8]([CH3:14])([CH3:13])[NH:9][CH2:10]2)=[CH:5][C:4]=1[OH:15].N1C=CN=C1.[CH:21]([Si:24](Cl)([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])([CH3:23])[CH3:22].O>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][C:8]([CH3:13])([CH3:14])[NH:9][CH2:10]2)=[CH:5][C:4]=1[O:15][Si:24]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:21]([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 139400Triisopropylsilyl chlorideHCID 68497066HCID 68497066, compound

Product 1

HCID 68495874HCID 68495874, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 224 (1.25 g, 6 mmol) in DCM (50 ml) was added imidazole (1.73 g, 25.4 mmol) and triisopropylsilyl chloride (2.71 ml, 12.7 mmol). The reaction mixture was stirred at rt for 22 h. Water (30 ml) and Chloroform (30 ml) were added. The layers separated and the aqueous layer extracted with chloroform (3×30 ml). The combined organic layers were washed with brine (30 ml), dried (MgSO4) and concentrated in vacuo. Purification by column chromatography eluting with EtOAc:MeOH:TEA; 10:1:01 afforded the title compound (1.78 g, 81%) as colourless oil. 1H NMR (270 MHz; CDCl3) 1.06 (18H, d, J=6.7 Hz, 6×CH3CH), 1.14 (6H, s, 2×CH3), 1.14-1.28 (3H, m, 3×CH), 2.51 (2H, s, CH2), 3.74 (3H, s, OCH3), 3.89 (2H, s, CH2), 6.46 (1H, s, CH), 6.51 (1H, s, CH). 13C NMR (67.5 MHz; CDCl3) 12.95 (CH3), 18.03 (CH3), 27.76 (CH), 41.17 (CH2), 43.97 (CH2), 48.78 (C(CH3)2), 55.56 (OCH3), 112.96 (CH), 117.39 (CH), 126.24 (C), 126.92 (C), 143.58 (C), 149.34 (C). LC/MS (ES+) tr=2.65 min, m/z 364.36 (M++H).

Workup

  1. customThe layers separated
  2. extractionthe aqueous layer extracted with chloroform (3×30 ml)
  3. washThe combined organic layers were washed with brine (30 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by column chromatography
  7. washeluting with EtOAc

Sources & evidence

ORD record
ord-aa4885f4372d4e8e90cfb49e3de27c86
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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