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

HRID 2036891Notes

Reaction equation

HRID 2036891 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].[CH:21]1([C:25](O)=[O:26])[CH2:24][CH2:23][CH2:22]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.C(N(CC)CC)C>[CH:21]1([C:25]([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:26])[CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 19494Cyclobutanecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 86656618HCID 86656618, compound

Product 1

HCID 866565922-(cyclobutylcarbonyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamideYield 65.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

200 mg of N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide, 80 mg of cyclobutan carboxylic acid, 111 mg HOBT, 276 mg EDC and 0.6 ml triethylamine are dissolved in 7 ml DMF and stirred overnight. The mixture is evaporated and the residue is purified by silica gel chromatography. 170 mg of a yellowish foam are obtained.

Workup

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

Sources & evidence

ORD record
ord-24717c4d5bf249158093e90d071f954b
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

Loading…