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

HRID 2036890Notes

Reaction equation

HRID 2036890 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].[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][C:28](O)=[O:29].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.C(N(CC)CC)C>[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][C:28]([N:16]1[CH2:15][CH2:14][C:13]2[C:18](=[CH: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]=2)[CH2:17]1)=[O:29]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 853182-Pyridineacetic acidHCID 86656618HCID 86656618, compound

Product 1

HCID 866565912-(pyridin-2-ylacetyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamideYield 40.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

200 mg of N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide, 69 mg of 2-pyridineacetic 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 treated with 5 ml water and 10 ml of dichloromethane. After separation, the water phase is washed with dichloromethane and the combined organic phases are filtered, dried and evaporated. 80 mg of a colorless oil are obtained.

Workup

  1. customThe mixture is evaporated
  2. additionthe residue is treated with 5 ml water and 10 ml of dichloromethane
  3. customAfter separation
  4. washthe water phase is washed with dichloromethane
  5. filtrationthe combined organic phases are filtered
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-7dadb2d47ed84c5aa7172f40ed0da6e1
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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