HCID 59831825, compound → HCID 59831627, compound

HRID 1716739Notes

Reaction equation

HRID 1716739 reaction equation
C(O[C:4](=[O:24])[CH2:5][CH:6]([C:13]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]2[C:14]=1[CH:15]=[N:16][NH:17]2)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.C(OC(=O)C=C(C1C=CC=C2C=1C(C#N)=[CH:40][NH:41]2)C1C=CC=CC=1)C>>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:13]([CH:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:5][C:4]([NH:41][CH3:40])=[O:24])=[C:14]2[C:18]=1[NH:17][N:16]=[CH:15]2

Participants

3

Reactant 2

HCID 59831825HCID 59831825, compoundHCID 673553223-(3-cyano-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester

Product 1

HCID 59831627HCID 59831627, compound

Procedure

3-(7-Methoxy-1H-indazol-4-yl)-N-methyl-3-phenyl-propionamide CXCIX was prepared from 3-(7-methoxy-1H-indazol-4-yl)-3-phenyl-propionic acid ethyl ester using the procedure described for preparation of 3-(1H-Indol-7-yl)-N-methyl-3-phenyl-acrylamide XVIII (see Example 4). Part of the crude 3-(7-Methoxy-1H-indazol-4-yl)-N-methyl-3-phenyl-propionamide CXCIX was used without further purification for the next step. A second portion of 3-(7-Methoxy-1H-indazol-4-yl)-N-methyl-3-phenyl-propionamide was purified on chiral HPLC by multiple injections onto 20×250 mm Chiralpak AD preparative column using a mixture of 70/30 hexane/EtOH at 7 ml/min in order to separate the enantiomers CXCIX-A and CXCIX-B.

Workup

  1. customPart of the crude 3-(7-Methoxy-1H-indazol-4-yl)-N-methyl-3-phenyl-propionamide CXCIX was used without further purification for the next step
  2. customA second portion of 3-(7-Methoxy-1H-indazol-4-yl)-N-methyl-3-phenyl-propionamide was purified on chiral HPLC by multiple injections onto 20×250 mm Chiralpak AD preparative column
  3. additiona mixture of 70/30 hexane/EtOH at 7 ml/min in order
  4. customto separate the enantiomers CXCIX-A and CXCIX-B

Sources & evidence

ORD record
ord-d089f7773a8542f09e69c0df94c59eac
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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