Trimethyl orthovalerate → HCID 12106184, compound

HRID 521252Notes

Reaction equation

HRID 521252 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][C:15]=1[NH2:24])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:25](OC)(OC)(OC)[CH2:26][CH2:27][CH2:28][CH3:29]>C1(C)C=CC=CC=1>[CH2:26]([C:25]1[N:13]([CH2:12][CH2:11][CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[C:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:24]=1)[CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 83755Trimethyl orthovalerateHCID 12106183HCID 12106183, compound

Product 1

HCID 12106184HCID 12106184, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N4-[4-(tert-butyldimethylsilanyloxy)butyl]quinoline-3,4-diamine (62.9 g, 182 mmol) and trimethyl orthovalerate (45.2 g, 278 mmol) in toluene (200 mL) was heated at reflux for 2 hours and then concentrated under reduced pressure to provide 2-butyl-1-[4-(tert-butyldimethylsilanyloxy)butyl]-1H-imidazo[4,5-c]quinoline as an oil that was used directly in the next step without further purification.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0a61164d4ed94beebc54ee1080171a00
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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