Thionyl Chloride → Methyl 2-(3-(((3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl)(3-chloropropyl)amino)methyl)phenyl)acetate

HRID 2090256Notes

Reaction equation

HRID 2090256 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:35][CH2:36][CH2:37][CH3:38])[N:14]([CH2:15][CH2:16][CH2:17][N:18]([CH2:23][C:24]3[CH:25]=[C:26]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:27]=[CH:28][CH:29]=3)[CH2:19][CH2:20][CH2:21]O)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.S(Cl)([Cl:41])=O>C(Cl)Cl>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:35][CH2:36][CH2:37][CH3:38])[N:14]([CH2:15][CH2:16][CH2:17][N:18]([CH2:23][C:24]3[CH:25]=[C:26]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:27]=[CH:28][CH:29]=3)[CH2:19][CH2:20][CH2:21][Cl:41])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68432245HCID 68432245, compound

Product 1

HCID 68430884Methyl 2-(3-(((3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl)(3-chloropropyl)amino)methyl)phenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the product from step (viii) (2.43 g) and thionyl chloride (10 mL) in DCM (30 mL) was stirred at rt for 4 h then evaporated under reduced pressure to give the subtitle compound. Used crude in next step.

Workup

  1. customthen evaporated under reduced pressure

Sources & evidence

ORD record
ord-3ed421f2a6834979824aeeac45688eef
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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