Trimethyl orthovalerate → HCID 46831677, compound

HRID 547324Notes

Reaction equation

HRID 547324 reaction equation
[C:1](OC)(OC)(OC)[CH2:2][CH2:3][CH2:4][CH3:5].Cl.N1C=CC=CC=1.[NH2:19][C:20]1[CH:21]=[N:22][C:23]2[C:28]([C:29]=1[NH:30][CH2:31][C:32]([CH3:35])([OH:34])[CH3:33])=[CH:27][CH:26]=[CH:25][CH:24]=2>C(#N)C>[CH2:2]([C:1]1[N:30]([CH2:31][C:32]([CH3:35])([OH:34])[CH3:33])[C:29]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:22]=[CH:21][C:20]=2[N:19]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 83755Trimethyl orthovalerateHCID 10176127Pyridinium chlorideHCID 149869411-((3-Aminoquinolin-4-yl)amino)-2-methylpropan-2-ol

Product 1

HCID 46831677HCID 46831677, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trimethyl orthovalerate (3.6 mL, 21 mmol) and pyridine hydrochloride (0.22 g, 1.9 mmol) were added to a solution of 1-[(3-aminoquinolin-4-yl)amino]-2-methylpropan-2-ol (prepared as described in Part A of Example 8, approximately 4.4 g, 19 mmol) in acetonitrile (96 mL). The reaction mixture was heated at reflux for 1 hour, then was allowed to cool to room temperature and was concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane) to yield 4.1 g of 1-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol as a white foam.

Workup

  1. customprepared
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 1 hour
  4. concentrationwas concentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-9c93a9833c7f4e72924f6f0e23ab916a
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

Loading…