Triethylamine → HCID 10024982, compound

HRID 1268811Notes

Reaction equation

HRID 1268811 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([NH2:19])[C:9]=2[N:8]=[C:7]1[CH2:20][CH2:21][O:22][CH3:23].C(N(CC)CC)C.Cl[CH2:32][CH2:33][CH2:34][S:35](Cl)(=[O:37])=[O:36].N12CCCN=C1CCCCC2>ClCCl.O>[O:36]=[S:35]1(=[O:37])[CH2:34][CH2:33][CH2:32][N:1]1[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([NH2:19])[C:9]=2[N:8]=[C:7]1[CH2:20][CH2:21][O:22][CH3:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 221808721-(4-aminobutyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 10024982HCID 10024982, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, 1-(4-aminobutyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine (500 mg, 1.6 mmol) was dissolved in dichloromethane (5 mL) and triethylamine (0.33 mL, 2.4 mmol). 3-Chloropropylsulfonyl chloride (0.19 mL, 1.6 mmol) was added dropwise and the reaction was stirred for 2 hours. The solvent was removed in vacuo. The residue was dissolved in N,N-dimethylformamide (5 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.48 mL, 3.2 mmol) was added. The reaction was stirred for 72 hours and then poured into water and extracted with dichloromethane. The organic layer was washed with water followed by brine; dried (Na2SO4); decanted and evaporated to yield crude product as a brown oil. Purification involved flash column chromatography (silica gel, gradient elution with methanol/dichloromethane 100:0 to 94:6) followed by recrystallization from acetonitrile to provide 289 mg of 1-[4-(1,1-dioxidoisothiazolidin-2-yl)butyl]-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a yellow crystalline solid, m.p. 156.4–157.7° C.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in N,N-dimethylformamide (5 mL)
  3. stirringThe reaction was stirred for 72 hours
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water
  6. dry with materialdried (Na2SO4)
  7. customdecanted
  8. customevaporated
  9. customto yield crude product as a brown oil
  10. customPurification
  11. washflash column chromatography (silica gel, gradient elution with methanol/dichloromethane 100:0 to 94:6)
  12. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-f62cc918dc4c4ddcaa58d3564176d60d
Source dataset
uspto-grants-2007_04
Patent number
US07199131B2

Reaction notes

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