Diisopropylethylamine → 3-[4-[4-(2-Amidino-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidin-1-yl]pyridin-3-yl]-2-propenoic acid ethyl ester dihydrochloride

HRID 412575Notes

Reaction equation

HRID 412575 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH:5]=[CH:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][O:20][C:21]2[CH:30]=[C:29]3[C:24]([CH2:25][CH2:26][NH:27][CH2:28]3)=[CH:23][CH:22]=2)[CH2:15][CH2:14]1)[CH3:2].C(N(C(C)C)CC)(C)C.[ClH:41].[N:42]1([C:47](N)=[NH:48])C=CC=N1>CN(C)C=O>[ClH:41].[ClH:41].[CH2:1]([O:3][C:4](=[O:31])[CH:5]=[CH:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][O:20][C:21]2[CH:30]=[C:29]3[C:24]([CH2:25][CH2:26][N:27]([C:47](=[NH:42])[NH2:48])[CH2:28]3)=[CH:23][CH:22]=2)[CH2:15][CH2:14]1)[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 696969403-[4-[4-(1,2,3,4-Tetrahydroisoquinolin-7-yloxymethyl)piperidin-1-yl]pyridin-3-yl]-2-propenoic acid ethyl ester

Product 1

HCID 696966163-[4-[4-(2-Amidino-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidin-1-yl]pyridin-3-yl]-2-propenoic acid ethyl ester dihydrochlorideYield 101.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[4-[4-(1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidin-1-yl]pyridin-3-yl]-2-propenoic acid ethyl ester (70 mg) in dimethylformamide (1 ml) were added diisopropylethylamine (0.032 ml) and 1H-pyrazole-1-carboxamidine hydrochloride (27 mg), and the mixture was stirred at room temperature for 12 hours. The solvent was evaporated and to the obtained residue was added diethyl ether and the supernatant was removed. This procedure was repeated twice and hydrogen chloride-ethanol solution was added to the obtained residue and insoluble material was removed. The solution was concentrated and dried under reduced pressure to give the title compound (50 mg).

Workup

  1. customThe solvent was evaporated and to the obtained residue
  2. additionwas added diethyl ether
  3. customthe supernatant was removed
  4. additionhydrogen chloride-ethanol solution was added to the obtained residue and insoluble material
  5. customwas removed
  6. concentrationThe solution was concentrated
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-c538dfc4119e4d7788125a597a2df218
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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