Imidazole → HCID 66702002, compound

HRID 729644Notes

Reaction equation

HRID 729644 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[NH2:14][C:15]1[N:20]=[C:19]([S:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=2[F:30])[N:18]=[C:17]([NH:31][C@H:32]([CH3:35])[CH2:33][OH:34])[CH:16]=1>CN(C=O)C>[Si:6]([O:34][CH2:33][C@H:32]([NH:31][C:17]1[CH:16]=[C:15]([NH2:14])[N:20]=[C:19]([S:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=2[F:30])[N:18]=1)[CH3:35])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 66702086HCID 66702086, compound

Product 1

HCID 66702002HCID 66702002, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (1.2 g) was added to a solution of tert-butyldimethylsilyl chloride (2.83 g) and the subtitle product of step iii) (1.8 g) in DMF (10 ml). The reaction was stirred for 20 h before partitioning between EtOAc (100 ml) and H2O (200 ml). The aqueous was extracted further with EtOAc (2×100 ml), the organics combined, washed with H2O (100 ml), brine (100 ml), dried (MgSO4) and concentrated in vacuo to a crude solid. This material was purified by column chromatography (50% Et2O/iso-hexane) to afford the subtitle compound as a yellow oil. Yield: 1.80 g.

Workup

  1. custombefore partitioning between EtOAc (100 ml) and H2O (200 ml)
  2. extractionThe aqueous was extracted further with EtOAc (2×100 ml)
  3. washwashed with H2O (100 ml), brine (100 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo to a crude solid
  6. customThis material was purified by column chromatography (50% Et2O/iso-hexane)

Sources & evidence

ORD record
ord-8e2d685fdff04f568cab83d1ed609bcd
Source dataset
uspto-grants-2009_09
Patent number
US07582644B2

Reaction notes

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