1,2-Dichloroethane → 4-(2-(Bis(isoquinolin-1-ylmethyl)amino)ethyl)benzenesulfonamide

HRID 56320

Reaction equation

HRID 56320 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[CH3:14][C:15](O)=O.[C:18]1([CH:28]=O)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][N:19]=1.[BH-](O[C:40]([CH3:42])=O)(OC(C)=O)OC(C)=O.[Na+].Cl[CH2:45][CH2:46]Cl>O>[C:18]1([CH2:28][N:1]([CH2:21][C:20]2[C:14]3[C:15](=[CH:45][CH:46]=[CH:40][CH:42]=3)[CH:27]=[CH:18][N:19]=2)[CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:8][CH:9]=2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][N:19]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 1696824-(2-Aminoethyl)benzenesulfonamideHCID 265306Isoquinoline-1-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 462339244-(2-(Bis(isoquinolin-1-ylmethyl)amino)ethyl)benzenesulfonamideYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-(2-aminoethyl)benzenesulfonamide (1.0 g, 5.0 mmol), AcOH (1.0 mL) and isoquinoline-1-carbaldehyde (2.09 g, 13.3 mmol) in DCE (50 mL) was stirred at 75° C. for 30 min under nitrogen. The reaction mixture was cooled to 0° C., and treated with NaBH(OAc)3 (3.165 g, 15 mmol). The reaction mixture was stirred at room temperature for overnight and decomposed with water. The reaction mixture was extracted with DCM. The organic layer was dried and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel to afford 4-(2-(bis(isoquinolin-1-ylmethyl)amino)ethyl)benzenesulfonamide (1.86 g, 77%). 1H NMR (400 MHz, DMSO-d6) 8.24 (d, J=8.8 Hz, 2H), 7.96 (d, J=8.4 Hz, 2H), 7.91 (d, J=8.0 Hz, 2H), 7.72 (t, J=7.8 Hz, 2H), 7.65 (d, J=8.4 Hz, 2H), 7.55 (t, J=7.6 Hz, 2H), 7.50 (d, J=8.4 Hz, 2H), 7.30 (d, J=6.0 Hz, 2H), 7.29 (s, 2H), 4.01 (s, 4H), 2.94 (t, J=7.0 Hz, 2H), 2.78 (t, J=7.0 Hz, 2H); MS (ESI), 483.3 (M+H)+.

Workup

  1. extractionThe reaction mixture was extracted with DCM
  2. customThe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-f95016a9fde44bfea8c494bb934bed02
Source dataset
uspto-grants-2016_09
Patent number
US09433594B2

Linked notes

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