Valeryl chloride → 3-(2-Butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl pentanoate

HRID 2090238Notes

Reaction equation

HRID 2090238 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[Si]([O:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][C:21]=1[NH2:30])(C(C)(C)C)(C)C>CN1C(=O)CCC1>[C:1]([O:15][CH2:16][CH2:17][CH2:18][N:19]1[C:20]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:23]=[CH:22][C:21]=2[N:30]=[C:1]1[CH2:2][CH2:3][CH2:4][CH3:5])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 61186Valeryl chlorideHCID 86647172N4-(3-(tert-Butyldimethylsilyloxy)propyl)quinoline-3,4-diamine

Product 1

HCID 684315713-(2-Butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl pentanoate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Valeryl chloride was added to a solution of the product from step (ii) (4.85 g) in NMP at rt. The mixture was stirred at rt for 15 min, heated at 100° C. for 6 h, cooled, and partitioned between EtOAc/saturated NaHCO3 solution. The organics were separated washed with water, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with EtOAc, yield 2.15 g.

Workup

  1. temperatureheated at 100° C. for 6 h
  2. temperaturecooled
  3. custompartitioned between EtOAc/saturated NaHCO3 solution
  4. customThe organics were separated
  5. washwashed with water
  6. customdried
  7. customevaporated under reduced pressure
  8. customThe residue was purified by chromatography on silica eluting with EtOAc, yield 2.15 g

Sources & evidence

ORD record
ord-c5857098546c4e9d85750894e8051ac8
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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