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

HRID 2036890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2036890
[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]

Komponenten

7

Edukt 4

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

Produkt 1

HCID 866565912-(pyridin-2-ylacetyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamideAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7dadb2d47ed84c5aa7172f40ed0da6e1
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575193B2

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