Sodium Methoxide → HCID 22254515, compound

HRID 433998Notes

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[CH2:31][CH2:32][CH2:33][CH3:34])[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[CH2:31][CH2:32][CH2:33][CH3:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 10942334Sodium Methoxide

HCID 22254524HCID 22254524, compound

Product 1

HCID 22254515HCID 22254515, compoundYield 7.3%

Procedure

Using the general method of example 1 Part D, N-{1-[2-(benzyloxy)ethyl]-2-butyl-1H-imidazo[4,5-c]quinolin-4-yl}-2,2,2-trichloroacetamide (3.3 g, 6.39 mmol) was hydrolyzed with sodium methoxide (5 mL of 25% in methanol). The resulting tan solid was purified by chromatography over silica gel (98/2 dichloromethane/methanol), recrystallized from methanol and dried under vacuum at 60° C. for 18 hours to provide 0.174 g of 1-[2-(benzyloxy)ethyl]-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, m.p. 133-135° C.

Workup

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

Sources & evidence

ORD record: ord-d3f4516d1b4844e491ec3c990cb45a3c
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06670372B2

Reaction notes

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