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

HRID 2036889Notes

Reaction equation

HRID 2036889 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[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

Participants

7

Reactant 4

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

Product 1

HCID 866565892-(1H-indol-3-ylacetyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamideYield 57.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-f57a3c05b9b846639344716c699c34cb
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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