3-(1H-Indol-7-yl)-N-methyl-3-phenyl-propionamide → HCID 59831718, compound

HRID 268885Notes

Reaction equation

HRID 268885 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[CH:13][C:14]([NH:16][CH3:17])=[O:15])=[CH:9][CH:10]=2)[NH:5][N:4]=1.N1C2C(=CC=CC=2C(C2C=CC=CC=2)CC(NC)=O)C=C1>>[CH3:1][O:2][C:3]1[C:11]2[C:6](=[CH:7][C:8]([CH:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:13][C:14]([NH:16][CH3:17])=[O:15])=[CH:9][CH:10]=2)[NH:5][N:4]=1

Participants

3

Reactant 2

HCID 598317453-(1H-Indol-7-yl)-N-methyl-3-phenyl-propionamideHCID 67355209HCID 67355209, compound

Product 1

HCID 59831718HCID 59831718, compound

Procedure

3-(3-Methoxy-1H-indazol-6-yl)-N-methyl-3-pyridin-2yl-propionamide CCXLVI was prepared from 3-(3-methoxy-1H-indazol-6-yl)-N-methyl-3-pyridin-2yl-acrylamide using the procedure described for preparation of 3-(1H-Indol-7-yl)-N-methyl-3-phenyl-propionamide XIX (Example 4). The crude product (90% yield) was purified via chiral preparative HPLC by multiple injections onto 20×250 mm Chiralpak AD preparative column using a mixture of 60/40 hexane/isopropanol at 7 ml/min affording the enatiomer CCXLVI-A (αD=−0.269°) and the enantiomer CCXLVI-B (αD=+0.209°).

Sources & evidence

ORD record
ord-ed38fafdd25b49939bd54f43a402d643
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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