HCID 22254529, compound → HCID 22254474, compound

HRID 433999Notes

Reaction equation

HRID 433999 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[C:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[C:15]([NH:24]C(=O)C(Cl)(Cl)Cl)[C:14]=2[N:13]=[C:12]1[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C[O-].[Na+]>[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[C:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[C:15]([NH2:24])[C:14]=2[N:13]=[C:12]1[CH3:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 22254529HCID 22254529, compound

Product 1

HCID 22254474HCID 22254474, compoundYield 14.2%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

Using the general method of example 1 Part D, N-{1-[2-(benzyloxy)ethyl]-2-methyl-1H-imidazo[4,5-c]quinolin-4-yl}-2,2,2-trichloroacetamide (10.46 g, 21.89 mmol) was hydrolyzed with sodium methoxide (20 mL of 25% in methanol). The resulting brown solid was purified by chromatography over silica gel (98/2 dichloromethane/methanol) and dried under vacuum at 60° C. for 18 hours to provide 1.036 g of 1-[2-(benzyloxy)ethyl]-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, m.p. 159-160° C.

Workup

  1. customThe resulting brown solid was purified by chromatography over silica gel (98/2 dichloromethane/methanol)
  2. customdried under vacuum at 60° C. for 18 hours

Sources & evidence

ORD record
ord-4097d9c780b149199273736ed8819df6
Source dataset
uspto-grants-2003_12
Patent number
US06670372B2

Reaction notes

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