1,2-Dichloroethane → 2-(3-pyridin-3-ylpropanoyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide

HRID 2036895Notes

Reaction equation

HRID 2036895 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:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH2:17][NH:16][CH2:15][CH2:14]2)=[O:10].N1C=CC=C(C[C:28](O)=[O:29])C=1.[CH:31]1[CH:32]=[CH:33][C:34]2N(O)N=[N:37][C:35]=2[CH:36]=1.[CH2:41](Cl)CCl>CN(C=O)C.C(N(CC)CC)C>[N:37]1[CH:35]=[CH:34][CH:33]=[C:32]([CH2:31][CH2:36][C:28]([N:16]2[CH2:15][CH2:14][C:13]3[C:18](=[CH: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]=3)[CH2:17]2)=[O:29])[CH:41]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 1083-Pyridineacetic acidHCID 757711-HydroxybenzotriazoleHCID 86656618HCID 86656618, compound

Product 1

HCID 866565972-(3-pyridin-3-ylpropanoyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamideYield 18.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 200 mg N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide, 109 mg 3-pyridylacetic acid, 111 mg HOBt, 276 mg EDC, 0.603 ml triethylamine and 7 ml DMF is stirred overnight. The reaction mixture is purified by silica gel chromatography. 55 mg of the title compound are obtained as nearly colorless foam.

Workup

  1. customThe reaction mixture is purified by silica gel chromatography

Sources & evidence

ORD record
ord-651e5751fe5549598446b764e9dbe232
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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