Imidazole → HCID 123427162, compound

HRID 711181Notes

Reaction equation

HRID 711181 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([OH:14])[CH:10]=[C:11]([Cl:13])[CH:12]=2)[N:5]=[C:4]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:3]=1.N1C=CN=C1.[C:24]([Si:28]([CH3:31])([CH3:30])Cl)([CH3:27])([CH3:26])[CH3:25]>CN(C=O)C.O>[C:15]([C:4]1[CH:3]=[C:2]([NH2:1])[N:6]([C:7]2[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([O:14][Si:28]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:31])[CH3:30])[CH:8]=2)[N:5]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride2×HCID 1177297543-(5-Amino-3-tert-butyl-pyrazol-1-yl)-5-chloro-phenol

Product 1

HCID 123427162HCID 123427162, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of Intermediate 62b (615 mg, 2.31 mmol) and imidazole (189 mg, 2.78 mmol) in DMF (4.5 mL) was added tert-butyl dimethylchlorosilane (384 mg, 2.55 mmol). The solution was stirred for 2 h then added tert-butyl dimethylchlorosilane (192 mg, 1.28 mmol). After 1.5 h, the solution was diluted with water and extracted with EtOAc. The combined organics were dried and concentrated in vacuo to give the title compound (831 mg, 94%). LCMS (Method 3): Rt 5.21 min, m/z 380 [MH+].

Workup

  1. waitAfter 1.5 h
  2. extractionextracted with EtOAc
  3. customThe combined organics were dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9afc32634e33406f8c4335d6d95c33ff
Source dataset
uspto-grants-2015_11
Patent number
US09181242B2

Reaction notes

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