Sodium Iodide → Methyl 2-(4-(((3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propyl)(3-morpholinopropyl)amino)methyl)phenyl)acetate

HRID 2090268Notes

Reaction equation

HRID 2090268 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:31][CH2:32][O: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.Cl.Cl[CH2:37][CH2:38][CH2:39][N:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1.C([O-])([O-])=O.[K+].[K+].[I-].[Na+]>CC#N>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:31][CH2:32][O: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)[CH2:37][CH2:38][CH2:39][N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[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 5238Sodium IodideHCID 11430Potassium CarbonateHCID 122962834-(3-Chloropropyl)morpholinium chlorideHCID 68430910Methyl 2-(4-((3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propylamino)methyl)phenyl)acetate

Product 1

HCID 25107233Methyl 2-(4-(((3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propyl)(3-morpholinopropyl)amino)methyl)phenyl)acetateYield 6.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product from step (v) of example 29 (360 mg, 0.78 mmol) was dissolved in MeCN (10 mL) and 4-(3-chloropropyl)morpholine hydrochloride (187 mg, 0.94 mmol) added at rt. Anhydrous K2CO3 (323 mg, 2.34 mmol) and sodium iodide (117 mg, 0.78 mmol) were added. The mixture was refluxed for 15 h. After cooling to room temperature, the crude product was purified by RPHPLC and the resulting residue was triturated with diethyl ether:EtOAc (5:1) at 0° C. The suspension was filtered to afford the title compound as a pale yellow solid (31 mg).

Workup

  1. temperatureThe mixture was refluxed for 15 h
  2. customthe crude product was purified by RPHPLC
  3. customthe resulting residue was triturated with diethyl ether:EtOAc (5:1) at 0° C
  4. filtrationThe suspension was filtered

Sources & evidence

ORD record
ord-1e5ec2fba0264ad7a84425e864870881
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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