Water → HCID 136174530, compound

HRID 415553Notes

Reaction equation

HRID 415553 reaction equation
CC(C)([O-])C.[K+].CS([C:11]1[N:12]([C@H:24]([CH3:38])[CH2:25][CH2:26][NH:27]C(=O)OCC2C=CC=CC=2)[C:13]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:23]=1)(=O)=O.C(Cl)Cl.O>C1COCC1>[CH3:38][C@@H:24]1[N:12]2[C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=[CH:15][C:14]=3[N:23]=[C:11]2[NH:27][CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 23665647Potassium tert-butoxide2×HCID 86633745HCID 86633745, compound

Product 1

HCID 136174530HCID 136174530, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (86 mg) was added to a solution of benzyl (3R)-3-[2-(methylsulfonyl)-1H-imidazo[4,5-c]quinolin-1-yl]butylcarbamate (380 mg, 0.84 mmol) in 10 mL of THF. The reaction was stirred for about two hours at room temperature, and an analysis by thin layer chromatography (TLC) indicated the presence of starting material. Additional potassium tert-butoxide (120 mg) was added, and the reaction was stirred over three days at room temperature. CH2Cl2 (20 mL) and H2O (20 mL) were added. The layers were separated, and the organic fraction was washed sequentially with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. Chromatography (SiO2, 10-30% CMA/CHCl3) afforded (11S)-11-methyl-8,9,10,11-tetrahydropyrimido[1′,2′:1,2]imidazo[4,5-c]quinoline (170 mg) as an off white solid.

Workup

  1. stirringthe reaction was stirred over three days at room temperature
  2. customThe layers were separated
  3. washthe organic fraction was washed sequentially with saturated NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f95553c219f4e059861c39c6cab786b
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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