1,2-Dichloroethane → HCID 86656614, compound

HRID 2036910Notes

Reaction equation

HRID 2036910 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].[CH3:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.C(N(CC)CC)C>[CH3:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([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:27])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 7470P-Toluic AcidHCID 757711-HydroxybenzotriazoleHCID 86656621N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-7-carboxamide

Product 1

HCID 86656614HCID 86656614, compoundYield 27%

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, 108 mg 4-methylbenzoic 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. The residue is purified by silica gel flash chromatography. 77 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-4c491f1a9e934902843cc9b71b2eeee6
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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