1,2-Dichloroethane → HCID 86656604, compound

HRID 2036900Notes

Reaction equation

HRID 2036900 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].C1C=CC2N([OH:30])N=NC=2C=1.[CH2:31](Cl)[CH2:32]Cl.C(N([CH2:40][CH3:41])CC)C.CN([CH:45]=[O:46])C>ClCCl.O>[O:46]1[CH2:40][CH2:41][CH:31]([C:32]([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:30])[CH2:45]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 86656618HCID 86656618, compound

Product 1

HCID 86656604HCID 86656604, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 200 mg N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide, 0.038 ml tetrahydrofuryl-3-carboxylic acid, 111 mg HOBt, 276 mg EDC, 0.603 ml triethylamine and 7 ml DMF is stirred overnight at ambient temperature. The reaction mixture is added to a mixture of 20 ml water and 50 ml dichloromethane. The water phase is washed twice with dichloromethane and the combined organic phases are dried and evaporated. The residue is then purified by silica gel chromatography. 176 mg of the title compound are obtained as colorless foam after drying.

Workup

  1. washThe water phase is washed twice with dichloromethane
  2. customthe combined organic phases are dried
  3. customevaporated
  4. customThe residue is then purified by silica gel chromatography

Sources & evidence

ORD record
ord-5c0b93a9c66c43f2ab4120535bf1b3a6
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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