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

HRID 2036889노트

반응식

HRID 2036889 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-f57a3c05b9b846639344716c699c34cb
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575193B2

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