1,2-Dichloroethane → N2-(2-phenylethyl)-N7-(tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroisoquinoline-2,7(1H)-dicarboxamide

HRID 2036909Notes

Reaction equation

HRID 2036909 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][NH:17][CH2:18]2)=[CH:13][CH:12]=1)=[O:10].[C:21]1([CH2:27][CH2:28][N:29]=[C:30]=[O:31])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.C(N(CC)CC)C>[C:21]1([CH2:27][CH2:28][NH:29][C:30]([N:17]2[CH2:16][CH2:15][C:14]3[C:19](=[CH:20][C:11]([C:9]([NH:8][O:7][CH:2]4[CH2:3][CH2:4][CH2:5][CH2:6][O:1]4)=[O:10])=[CH:12][CH:13]=3)[CH2:18]2)=[O:31])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 160602Phenethyl isocyanateHCID 86656621N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-7-carboxamide

Product 1

HCID 86656613N2-(2-phenylethyl)-N7-(tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroisoquinoline-2,7(1H)-dicarboxamideYield 67.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 200 mg N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-7-carboxamide, 117 mg phenylethyl-isocyanat, 98 mg HOBt, 278 mg EDC, 0.6 ml triethylamine and 8 ml DMF is stirred overnight at ambient temperature. The mixture is evaporated. The residue is purified by silica gel flash chromatography. 208 mg of the title compound are obtained after drying as colorless foam.

Workup

  1. customThe mixture is evaporated
  2. customThe residue is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-4e7dcf35fadc4c2db3c5c3e3a240e9fe
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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