Imidazole → HCID 86602455, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]([N:11]([CH3:13])[CH3:12])=[O:10])=[C:4]([NH:14][C@H:15]([OH:18])[CH2:16][OH:17])[N:3]=1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].N1C=CN=C1>CN(C=O)C>[Si:19]([O:17][CH2:16][C@H:15]([NH:14][C:4]1[C:5]([C:9]([N:11]([CH3:13])[CH3:12])=[O:10])=[C:6]([Cl:8])[N:7]=[C:2]([Cl:1])[N:3]=1)[OH:18])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of the subtitle product of step iv) (0.50 g) in DMF (10 ml) was added tert-butyldimethylsilyl chloride (0.51 g) at −10° C. in portions. To this mixture was then added imidazole in portions. The mixture was then stirred at 0° C. for 1 h and allowed to come to room temperature and stirred for 16 h. The mixture was quenched with water and extracted with EtOAc (2×250 ml). The combined organics were washed with water (3×20 ml) and brine (3×20 ml), the organic layer dried (MgSO4) and the solid filtered. The filtrate was evaporated to dryness and the residue chromatographed on silica gel eluting with EtOAc/isohexane (1:1) to yield the subtitle compound as an oil. Yield 1.0 g.
Workup
- customto come to room temperature
- stirringstirred for 16 h
- customThe mixture was quenched with water
- extractionextracted with EtOAc (2×250 ml)
- washThe combined organics were washed with water (3×20 ml) and brine (3×20 ml)
- dry with materialthe organic layer dried (MgSO4)
- filtrationthe solid filtered
- customThe filtrate was evaporated to dryness
- customthe residue chromatographed on silica gel eluting with EtOAc/isohexane (1:1)
Sources & evidence
- ORD record
- ord-5ae78514e51c47a5978c9a260e396988
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07482355B2
Reaction notes
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