Imidazole → N2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-methoxy-quinoline-2,6-diamine

HRID 1773565Notes

Reaction equation

HRID 1773565 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([NH:14][CH2:15][CH2:16][OH:17])[CH:6]=[CH:5]2.[C:18]([Si:22]([CH3:25])([CH3:24])Cl)([CH3:21])([CH3:20])[CH3:19].N1C=CN=C1>ClCCl>[C:18]([Si:22]([CH3:25])([CH3:24])[O:17][CH2:16][CH2:15][NH:14][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:2]([NH2:1])[CH:3]=2)[N:8]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 580562842-(6-Amino-7-methoxy-quinolin-2-ylamino)-ethanol

Product 1

HCID 68090908N2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-methoxy-quinoline-2,6-diamineYield 34.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(6-amino-7-methoxy-quinolin-2-ylamino)-ethanol (0.4 g, 1.72 mmol), tert-butyldimethylchlorosilane (0.8 g, 5.15 mmol) and imidazole (0.4 g, 5.15 mmol) in dichloromethane (20 mL) was stirred at room temperature for 62 hours. The resulting mixture was washed with water and the organic layer was separated, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexane, 3/7) to afford 206 mg of N2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-methoxy-quinoline-2,6-diamine as a brown oil. MS=348 [M+H]+.

Workup

  1. washThe resulting mixture was washed with water
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude residue was purified by flash chromatography (EtOAc/hexane, 3/7)

Sources & evidence

ORD record
ord-aad0f8ce84f845ad9540eaf6c3d6fb95
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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