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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 2090262
Notes
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Reaction equation

HRID 2090262 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 25106601Methyl 2-(4-((3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propylamino)methyl)phenyl)acetate

Product 1

HCID 59563513Methyl 2-(4-((N-(3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl)acetamido)methyl)phenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. customThe solvents were evaporated
  2. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes