Imidazole → HCID 86660293, compound

HRID 244279Notes

Reaction equation

HRID 244279 reaction equation
[OH:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[N:12]1[CH2:17][CH2:16][CH:15]([C:18]([N:20]([O:22][CH3:23])[CH3:21])=[O:19])[CH2:14][CH2:13]1.N1C=CN=C1.[CH3:29][C:30]([Si:33](Cl)([CH3:35])[CH3:34])([CH3:32])[CH3:31]>C(Cl)Cl>[Si:33]([O:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[N:12]1[CH2:13][CH2:14][CH:15]([C:18]([N:20]([O:22][CH3:23])[CH3:21])=[O:19])[CH2:16][CH2:17]1)([C:30]([CH3:32])([CH3:31])[CH3:29])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86660294HCID 86660294, compound

Product 1

HCID 86660293HCID 86660293, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 22 (400 mg, 1.25 mmol) and imidazole (400 mg) in CH2Cl2 (50 mL), TBDMSCl (2.5 mmol) was added. The reaction mixture was stirred overnight at room temperature until TLC indicated that the reaction was complete. The reaction mixture was washed by brine and 1M NaH2PO4 (30 mL×3). The organic layer was dried and concentrated to a residue. The crude product was purified with column chromatography to afforded 23 (400 mg, 70%). 1H NMR (CDCl3,): δ 0.12 (s, 6H), 0.91 (s, 9H), 1.65-1.77 (m, 4H), 2.46-3.05 (m, 9H), 3.17 (s, 3H), 3.69 (s, 3H), 4.13 (br, 2H), 7.04-7.12 (m, 4H).

Workup

  1. washThe reaction mixture was washed by brine and 1M NaH2PO4 (30 mL×3)
  2. customThe organic layer was dried
  3. concentrationconcentrated to a residue
  4. customThe crude product was purified with column chromatography

Sources & evidence

ORD record
ord-6d0294c2869745a084441b663a732ae0
Source dataset
uspto-grants-2014_02
Patent number
US08658131B2

Reaction notes

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