Imidazole → HCID 178455472, compound

HRID 1873948Notes

Reaction equation

HRID 1873948 reaction equation
Cl.[CH:2]1([C:6]2[C:14]3[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=3)[NH:8][N:7]=2)[CH2:5][CH2:4][CH2:3]1.N1C=CN=C1.[CH3:21][C:22]([Si:25](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:24])[CH3:23].O>CN(C=O)C>[Si:25]([O:15][C:11]1[CH:10]=[C:9]2[C:14]([C:6]([CH:2]3[CH2:3][CH2:4][CH2:5]3)=[N:7][NH:8]2)=[CH:13][CH:12]=1)([C:22]([CH3:24])([CH3:23])[CH3:21])([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 178479617HCID 178479617, compound

Product 1

HCID 178455472HCID 178455472, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Cyclobutylindazol-6-ol hydrochloride (6.45 g) which can be prepared according to the method described in Reference example 11, etc. and imidazole (5.039 g) were dissolved in DMF (100 mL; manufactured by Kanto Chemical Co., Inc.). Then, TBDPSCl (18.44 mL) was added and the mixture was stirred overnight at room temperature. To the reaction solution, water was added and extraction was carried out twice with ethyl acetate. The organic layer was washed twice with water and once with brine and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=95:5→74:26) to obtain the title compound (9.93 g).

Workup

  1. extractionextraction
  2. washThe organic layer was washed twice with water and once with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter the solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=95:5→74:26)

Sources & evidence

ORD record
ord-1dd12aeb759c452fa719a9a9693aed1c
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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