Indole-3-Acetic Acid → 2-(1H-indol-3-ylacetyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide

HRID 2036889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2036889
[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[CH:26]=[C:25]2[C:27]([CH2:30][C:31](O)=[O:32])=[CH:28][NH:29][C:24]2=[CH:23][CH:22]=1.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.C(Cl)CCl>[NH:29]1[C:24]2[C:25](=[CH:26][CH:21]=[CH:22][CH:23]=2)[C:27]([CH2:30][C:31]([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:32])=[CH:28]1

Komponenten

7

Edukt 4

HCID 802Indole-3-Acetic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 86656618HCID 86656618, Verbindung

Produkt 1

HCID 866565892-(1H-indol-3-ylacetyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamideAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

200 mg of N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide, 140 mg Indolyl-3-acetic acid, 98 mg HOBT and 0.6 ml Et3N are dissolved in 8 ml DMF. To this mixture are added 278 mg EDC and the mixture is stirred overnight. The reaction mixture is evaporated and the crude product is purified by silica gel flash chromatography. 180 mg of the title compound are obtained in 57% yield.

Aufarbeitung

  1. customThe reaction mixture is evaporated
  2. customthe crude product is purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f57a3c05b9b846639344716c699c34cb
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575193B2

Notizen zur Reaktion

Wird geladen…