Sodium Methoxide → HCID 10269444, compound

HRID 432694Notes

Reaction equation

HRID 432694 reaction equation
ClC(Cl)(Cl)C([NH:5][C:6]1[C:15]2[N:16]=[CH:17][N:18]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1)=O.C[O-].[Na+]>>[S:26]1[CH:27]=[CH:28][CH:29]=[C:25]1[CH2:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][N:18]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH2:5])[C:15]=2[N:16]=[CH:17]1

Participants

3

Reactant 2

HCID 10942334Sodium MethoxideHCID 18760171HCID 18760171, compound

Product 1

HCID 10269444HCID 10269444, compound

Procedure

A dried round bottom flask was charged with a stir bar, 2,2,2-trichloro-N-{1-[2-(3-thien-2-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-yl}acetamide and sodium methoxide (25% in methanol, 11 mL, 49.8 mmol) at ambient temperature. The reaction was judged complete after 30 hours. The volatiles were removed under reduced pressure. The resulting oil was purified with chromatography over silica gel (95/5 dichloromethane/methanol), semi-preparative HPLC using method A, and recrystallization from ethyl acetate/hexane to provide 43 mg of 1-[2-(3-thien-2-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine as a white crystalline solid. m.p. 130.1-131.6° C.

Workup

  1. additionA dried round bottom flask was charged with a stir bar
  2. customat ambient temperature
  3. customThe volatiles were removed under reduced pressure
  4. customThe resulting oil was purified with chromatography over silica gel (95/5 dichloromethane/methanol), semi-preparative HPLC
  5. custommethod A, and recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-9b35067d6f5140309491b15cb98836ec
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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