Imidazole → 1-((5-(tert-butyldimethylsilyloxy)-6-methylpyridin-2-yl)methyl)-3-cyclopropyl-1H-indazol-4-amine

HRID 79485Notes

Reaction equation

HRID 79485 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:20]1[CH2:22][CH2:21]1)=[N:5][N:6]2[CH2:11][C:12]1[N:17]=[C:16]([CH3:18])[C:15]([OH:19])=[CH:14][CH:13]=1.[C:23]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])([CH3:25])[CH3:24].N1C=CN=C1>CN(C=O)C>[Si:27]([O:19][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[C:2]([NH2:1])[C:3]=3[C:4]([CH:20]3[CH2:22][CH2:21]3)=[N:5]2)=[N:17][C:16]=1[CH3:18])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67251409HCID 67251409, compound

Product 1

HCID 672532771-((5-(tert-butyldimethylsilyloxy)-6-methylpyridin-2-yl)methyl)-3-cyclopropyl-1H-indazol-4-amineYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 6-((4-amino-3-cyclopropyl-1H-indazol-1-yl)methyl)-2-methylpyridin-3-ol (100 mg, 0.340 mmol) in DMF (5 mL) was added tert-butylchlorodimethylsilane (66.6 mg, 0.442 mmol) and 1H-imidazole (116 mg, 1.70 mmol). The reaction mixture was stirred for 18 hours at ambient temperature. The solvent was removed under reduced pressure, and the residue was purified by silica gel flash chromatography (1:4 EtOAc/hexanes) to give final product (97%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by silica gel flash chromatography (1:4 EtOAc/hexanes)

Sources & evidence

ORD record
ord-df39c32a0a9d4cb19b011c976eb96a43
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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