Imidazole → HCID 86602451, compound
Reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([NH:10][C@H:11]([CH3:14])[CH2:12][OH:13])[N:5]=[C:4]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=2[F:24])[N:3]=1.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].N1C=CN=C1>CN(C=O)C>[Si:25]([O:13][CH2:12][C@H:11]([NH:10][C:6]1[C:7]([CH:8]=[O:9])=[C:2]([Cl:1])[N:3]=[C:4]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=2[F:24])[N:5]=1)[CH3:14])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of the subtitle product of step i) (5.60 g) in DMF was added tert-butyldimethylsilyl chloride (2.40 g) at −10° C. in portions. To this mixture was then added imidazole in portions. The mixture was then stirred at 0° C. for 2 h before being quenched with excess water. The mixture was then extracted with EtOAc (2×250 ml), the combined organics washed with water (3×300 ml) and brine (2×30 ml). The organic layer was dried (MgSO4) and solid was filtered. The filtrate was evaporated to dryness. The residue was purified by column chromatography (10% EtOAc/isohexane) to yield the subtitle compound as a white solid.
Workup
- custombefore being quenched with excess water
- extractionThe mixture was then extracted with EtOAc (2×250 ml)
- washthe combined organics washed with water (3×300 ml) and brine (2×30 ml)
- dry with materialThe organic layer was dried (MgSO4) and solid
- filtrationwas filtered
- customThe filtrate was evaporated to dryness
- customThe residue was purified by column chromatography (10% EtOAc/isohexane)
Sources & evidence
- ORD record
- ord-023546adb5ac419c82aac8be098500f4
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07482355B2
Reaction notes
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