N,N-bis(3-aminopropyl)methylamine → N-(3-((3-aminopropyl)(methyl)amino)propyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide

HRID 45741

Reaction equation

HRID 45741 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([CH3:10])[CH2:6][CH2:7][CH2:8][NH2:9].C(N(CC)CC)C.[Cl:18][C:19]1[CH:20]=[C:21]2[C:26](=[C:27]([Cl:29])[CH:28]=1)[CH2:25][N:24]([CH3:30])[CH2:23][CH:22]2[C:31]1[CH:32]=[C:33]([S:37](Cl)(=[O:39])=[O:38])[CH:34]=[CH:35][CH:36]=1>C(Cl)Cl>[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([CH3:10])[CH2:6][CH2:7][CH2:8][NH:9][S:37]([C:33]1[CH:34]=[CH:35][CH:36]=[C:31]([CH:22]2[C:21]3[C:26](=[C:27]([Cl:29])[CH:28]=[C:19]([Cl:18])[CH:20]=3)[CH2:25][N:24]([CH3:30])[CH2:23]2)[CH:32]=1)(=[O:39])=[O:38]

Participants

5

Reactant 3

HCID 7777N,N-bis(3-aminopropyl)methylamineHCID 8471TriethylamineHCID 866723303-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride

Product 1

HCID 70872028N-(3-((3-aminopropyl)(methyl)amino)propyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamideYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N1-(3-aminopropyl)-N1-methylpropane-1,3-diamine (560 mg, 3.85 mmol) dissolved in DCM (20 mL), was added triethylamine (300 mg, 2.96 mmol) and 3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride (300 mg, 0.77 mmol). The resulting solution was stirred for 3 h at room temperature. After removing the solvent, the resulting residue was diluted with EtOAc (50 mL), washed with water (2×10 mL) and dried over anhydrous sodium sulfate. The crude product was purified by Flash-Prep-HPLC with H2O:MeOH (1:4) to afford 300 mg (74%) of N-(3-((3-aminopropyl)(methyl)amino)propyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide as a yellow oil.

Workup

  1. customAfter removing the solvent
  2. additionthe resulting residue was diluted with EtOAc (50 mL)
  3. washwashed with water (2×10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe crude product was purified by Flash-Prep-HPLC with H2O:MeOH (1:4)

Sources & evidence

ORD record
ord-7589c8bb860f4c9a8a66b2946edaff49
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Linked notes

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