1,2-Dichloroethane → 3-(dimethylamino)-N-(isoquinolin-6-yl)-2-(thiophen-3-yl)propanamide

HRID 1690256Notes

Reaction equation

HRID 1690256 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][CH:4]([C:8]1[CH:12]=[CH:11][S:10][CH:9]=1)[C:5]([OH:7])=O.C(Cl)CCl.[NH2:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[N:24][CH:23]=[CH:22]2.C([O-])(O)=O.[Na+]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:13][N:2]([CH3:1])[CH2:3][CH:4]([C:8]1[CH:12]=[CH:11][S:10][CH:9]=1)[C:5]([NH:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[N:24][CH:23]=[CH:22]2)=[O:7]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 516892Sodium BicarbonateHCID 5889916-AminoisoquinolineHCID 591617463-(Dimethylamino)-2-(thiophen-3-yl)propanoic acid

Product 1

HCID 446024983-(dimethylamino)-N-(isoquinolin-6-yl)-2-(thiophen-3-yl)propanamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To 3-(dimethylamino)-2-(thiophen-3-yl)propanoic acid (E43) in pyridine was added EDC, DMAP, and 6-aminoisoquinoline. The solution was stirred overnight at room temperature. The mixture was poured into NaHCO3 (sat) and extracted with EtOAc. The organics were dried (Na2SO4), filtered, and evaporated. Column chromatography (SiO2, 5-20% MeOH/CH2Cl2) gave pure 3-(dimethylamino)-N-(isoquinolin-6-yl)-2-(thiophen-3-yl)propanamide. The pure compound was taken up in CH2Cl2 and HCl was added. The solvents were evaporated to give pure 3-(dimethylamino)-N-(isoquinolin-6-yl)-2-(thiophen-3-yl)propanamide dihydrochloride (E44).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organics were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-3b17573e4d754b8d80a816b5b17cbe8e
Source dataset
uspto-grants-2012_04
Patent number
US08153656B2

Reaction notes

Loading…