1,2-Dichloroethane → N-(3-cyanobenzyl)-2N-(4-chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

HRID 1432541Notes

Reaction equation

HRID 1432541 reaction equation
ClC1C=CC(NC([CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH:13]([C:21]([OH:23])=O)[NH:12]2)=O)=CC=1.[C:24]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][NH2:30])#[N:25].[CH2:34]([Cl:37])[CH2:35]Cl.[OH2:38]>CN(C=O)C.CCOC(C)=O.CO.C(Cl)Cl.CCOC(C)=O>[C:24]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][NH:30][C:21]([CH:13]1[CH2:14][C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][N:12]1[C:11]([NH:12][C:13]1[CH:21]=[CH:35][C:34]([Cl:37])=[CH:15][CH:14]=1)=[O:38])=[O:23])#[N:25]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 457594Benzonitrile, 3-(aminomethyl)-HCID 131727716(4-Chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 86606516N-(3-cyanobenzyl)-2N-(4-chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 21901258Dichloromethane ethyl acetate methanolSolvent

Procedure

To a solution of 2N-(4-chlorophenylaminocarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (291 mg, 0.880 mmol) and 3-cyanobenzylamine (140 mg, 1.06 mmol) in DMF (7 mL), EDC (254 mg, 1.32 mmol) was added. The mixture was then stirred at room temperature overnight. H2O and EtOAc were added. The organic layer was separated, washed with 1N HCl, dried over Na2SO4, concentrated in vacuo to give a solid. After being trituated with EtOAc/MeOH/CH2Cl2, the white solid was collected, dried on vacuum (148 mg), which was pure enough for the next reaction.

Workup

  1. customThe organic layer was separated
  2. washwashed with 1N HCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a solid
  6. customthe white solid was collected
  7. customdried on vacuum (148 mg), which
  8. customwas pure enough for the next reaction

Sources & evidence

ORD record
ord-83afb3a3ec9a4e74a4f0d8c940da6a62
Source dataset
uspto-grants-2009_11
Patent number
US07612089B2

Reaction notes

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