Imidazole → HCID 58299853, compound

HRID 875941Notes

Reaction equation

HRID 875941 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]2)=[CH:4][CH:3]=1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].N1C=CN=C1>CN(C=O)C>[Si:14]([O:13][C@@H:10]1[CH2:11][CH2:12][N:8]([C:5]2[N:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:9]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 58299823(3R)-1-(6-Chloro-3-pyridazinyl)-3-pyrrolidinol

Product 1

HCID 58299853HCID 58299853, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 27 (815 mg, 4.08 mmol) in DMF (15 mL) were added t-butyldimethylsilyl chloride (738 mg, 4.9 mmol) and imidazole (556 mg, 8.16 mmol). The thus obtained solution was stirred at room temperature for 6 h. The reaction mixture was concentrated and the residue was purified by chromatography on silica gel eluting with 15% to 50% to give the compound 28 as a white solid (1.087 g, 85%). LCMS-ESI (POS), M/Z, M+1: Found 314.1, Calculated 314.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography on silica gel eluting with 15% to 50%

Sources & evidence

ORD record
ord-f105ab919a4e49f2862aff867a03decf
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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