Imidazole → HCID 86731586, compound
Reaction equation
N1C=CN=C1.[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][OH:16])=[CH:9][CH:8]=1.[C:17]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])([CH3:19])[CH3:18]>O1CCCC1>[Si:21]([O:16][CH2:15][CH2:14][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([NH2:6])=[CH:12][CH:11]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:23])[CH3:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a 50 mL round bottomed flask was added 1H-imidazole (59.4 mg, 0.873 mmol), 3-(4-aminophenyl)propan-1-ol 120 mg, 0.794 mmol) and Tetrahydrofuran (THF) (5 mL). To this solution was added tert-butylchlorodimethylsilane (132 mg, 0.873 mmol), and this was left to stir for 2 days, under nitrogen at room temperature. Another 0.5 eq of tert-butylchlorodimethylsilane was added to the reaction and the reaction was left to stir for another 2 hours. After this, reaction was stopped and the suspension concentrated down on a Biotage V10 evaporator, and then the product extracted to the organic phase of an aqueous work up between ethyl acetate (10 mL) and water (10 mL). The organic phase was then passed through a hydrophobic frit, and concentrated in vacuo, leaving the crude product (212 mg, 100%). LCMS (M+1): 266, RT 1.14 mins.
Workup
- waitthis was left
- waitthe reaction was left
- stirringto stir for another 2 hours
- customAfter this, reaction
- concentrationthe suspension concentrated down on a Biotage V10 evaporator
- extractionthe product extracted to the organic phase of an aqueous work up between ethyl acetate (10 mL) and water (10 mL)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c7946ff0dd054ffcad7269662e2c8ba1
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150508B2
Reaction notes
Loading…