Valeryl chloride → 2-Butyl-1-(3-(tert-butyldimethylsilyloxy)propyl)-1H-imidazo[4,5-c]quinoline

HRID 2090253Notes

Reaction equation

HRID 2090253 reaction equation
[C:1](Cl)(=O)[CH2:2][CH2:3][CH2:4][CH3:5].[Si:8]([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:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]>CN1C(=O)CCC1>[CH2:2]([C:1]1[N:19]([CH2:18][CH2:17][CH2:16][O:15][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])[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]=1)[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 684291242-Butyl-1-(3-(tert-butyldimethylsilyloxy)propyl)-1H-imidazo[4,5-c]quinoline

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Pentanoyl chloride (3.7 mL) was added dropwise to a stirred solution of the product from step (iii) (10 g) and TEA (5 mL) in NMP (110 mL) at rt under nitrogen. The mixture was stirred at rt for 2 h then heated to 100° C. for 6 h. After cooling, the reaction mixture was partitioned between diethyl ether/water, the organics were separated, washed with water, dried, and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 50-70% EtOAc/isohexane, yield 6.58 g.

Workup

  1. temperaturethen heated to 100° C. for 6 h
  2. temperatureAfter cooling
  3. customthe reaction mixture was partitioned between diethyl ether/water
  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 50-70% EtOAc/isohexane, yield 6.58 g

Sources & evidence

ORD record
ord-902a67e700504e08846e228101561cd7
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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