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

HRID 2090235Notes

Reaction equation

HRID 2090235 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(Cl)Cl.Cl.[CH3:39][N:40]([CH3:45])[CH2:41][C:42](Cl)=[O:43].CCN(CC)CC>CN(C=O)C>[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:42](=[O:43])[CH2:41][N:40]([CH3:45])[CH3:39])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471Triethylamine2×HCID 139949912-(Dimethylamino)acetyl chloride hydrochloride2×HCID 25106601Methyl 2-(4-((3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propylamino)methyl)phenyl)acetate

Product 1

HCID 25052655Methyl 2-(4-((N-(3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl)-2-(dimethylamino)acetamido)methyl)phenyl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from example 1 (15 mg) was dissolved in a mixture of DMF:DCM, 1:1 (5 mL) and N,N-dimethylglycyl chloride hydrochloride salt (8 mg) and Et3N (0.01 mL) were added. The reaction mixture was stirred for 72 h. More N,N-dimethylglycyl chloride hydrochloride salt (0.050 g) and Et3N (0.06 mL) were added, the mixture was stirred for a further 16 h. The product was purified via RPHPLC.

Workup

  1. stirringthe mixture was stirred for a further 16 h
  2. customThe product was purified via RPHPLC

Sources & evidence

ORD record
ord-2132bd72484b40c89134ddbbd15f458a
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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