Acetyl chloride → Methyl 2-(4-((N-(3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl)acetamido)methyl)phenyl)acetate

HRID 2090262Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:31][CH2:32][CH2:33][CH3:34])[N:14]([CH2:15][CH2:16][CH2:17][NH:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:22][CH:21]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[C:35](Cl)(=[O:37])[CH3:36]>C(Cl)Cl>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:31][CH2:32][CH2:33][CH3:34])[N:14]([CH2:15][CH2:16][CH2:17][N:18]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:24][CH:25]=3)[C:35](=[O:37])[CH3:36])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The product from example 1 (142 mg) was dissolved in DCM (5 mL) and TEA (0.065 mL) was added. The reaction mixture was cooled to 0° C. Acetyl chloride (0.029 mL) was added and the reaction mixture stirred for 30 min. The solvents were evaporated and the residue was taken up in MeOH and purified by RPHPLC to afford the title compound (40 mg) as a white solid.

Workup

customThe solvents were evaporated
custompurified by RPHPLC

Sources & evidence

ORD record: ord-9ac6292cbc7d4d809839eb0e502529de
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436178B2

Reaction notes

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