3-(1H-Indol-7-yl)-N-methyl-3-phenyl-propionamide → HCID 67356826, compound

HRID 268878Notes

Reaction equation

HRID 268878 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][C:12]([NH:14][CH3:15])=[O:13])[CH:8]=2)[CH:3]=[N:2]1.N1C2C(=CC=CC=2C(C2C=CC=CC=2)CC(NC)=O)C=C1>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:11][C:12]([NH:14][CH3:15])=[O:13])[CH:8]=2)[CH:3]=[N:2]1

Participants

3

Reactant 2

HCID 598317453-(1H-Indol-7-yl)-N-methyl-3-phenyl-propionamideHCID 67356629HCID 67356629, compound

Product 1

HCID 67356826HCID 67356826, compound

Procedure

3-(1H-Indazol-6-yl)-N-methyl-3-phenyl-propionamide CCXXIX was prepared from 3-(1H-indazol-6-yl)-N-methyl-3-phenyl-acrylamide using the procedure described for preparation of 3-(1H-Indol-7-yl)-N-methyl-3-phenyl-propionamide XIX (Example 4). A portion of the 3-(1H-Indazol-6-yl)-N-methyl-3-phenyl-propionamide CCXXIX was used without further purification in the next step, while a portion was purified via chiral preparative HPLC. The two enantiomers CCXXIX-A and CCXXIX-B were separated by multiple injections onto 50×500 mm Chiralpak AD preparative column using a mixture of 85/15 hexane/isopropanol at 50 ml/minute.

Workup

  1. customA portion of the 3-(1H-Indazol-6-yl)-N-methyl-3-phenyl-propionamide CCXXIX was used without further purification in the next step, while a portion
  2. customwas purified via chiral preparative HPLC
  3. customThe two enantiomers CCXXIX-A and CCXXIX-B were separated by multiple injections onto 50×500 mm Chiralpak AD preparative column
  4. additiona mixture of 85/15 hexane/isopropanol at 50 ml/minute

Sources & evidence

ORD record
ord-d790a51360724cc6a43ddc2afedb6286
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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