1,2-Dichloroethane → 2-but-2-ynoyl-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-7-carboxamide

HRID 2036904Notes

Reaction equation

HRID 2036904 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](O)(=[O:25])[C:22]#[C:23][CH3:24].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.C(N(CC)CC)C>[C:21]([N:17]1[CH2:16][CH2:15][C:14]2[C:19](=[CH:20][C:11]([C:9]([NH:8][O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)=[O:10])=[CH:12][CH:13]=2)[CH2:18]1)(=[O:25])[C:22]#[C:23][CH3:24]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 685352-Butynoic acidHCID 757711-HydroxybenzotriazoleHCID 86656621N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-7-carboxamide

Product 1

HCID 866566062-but-2-ynoyl-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-7-carboxamideYield 52.5%

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, 67 mg butynoic acid, 98 mg HOBt, 278 mg EDC, 0.6 ml triethylamine and 8 ml DMF is stirred overnight at ambient temperature. The mixture is evaporated and the residue is purified by silica gel flash chromatography. 130 mg of a colorless foam are obtained after drying.

Workup

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

Sources & evidence

ORD record
ord-aedd495d984e4619a3fe6919f46a9a83
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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