1H-Indazole-3-carboxylic acid (4-benzyloxy-phenyl)-amide → 1H-Indazole-3-carboxylic acid (4-hydroxy-phenyl)-amide

HRID 2238286Notes

Reaction equation

HRID 2238286 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][N:19]=2)=[O:17])=[CH:11][CH:10]=1)C1C=CC=CC=1.OC1C=CC(NC([C@@H]2CCCN2)=O)=CC=1>>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][N:19]=2)=[O:17])=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 93142921H-Indazole-3-carboxylic acid (4-benzyloxy-phenyl)-amideHCID 11390123(S)-Pyrrolidine-2-carboxylic acid (4-hydroxy-phenyl)-amide

Product 1

HCID 112075071H-Indazole-3-carboxylic acid (4-hydroxy-phenyl)-amide

Procedure

This compound was prepared from 1H-Indazole-3-carboxylic acid (4-benzyloxy-phenyl)-amide, using the same method used to prepare (S)-pyrrolidine-2-carboxylic acid (4-hydroxy-phenyl)-amide. The product was purified by flash chromatography, on silica gel, eluted with 5 to 10% methanol in DCM, to give the product as an off white solid, 2.6 g (60% for 2 steps). MS m/z 254 (MH+). 1H NMR(DMSO-d6) δ 6.74 (d, 2H), 7.26-7.34 (m, 1H), 7.43-7.51 (m, 1H), 7.67-7.73 (m, 3H), 8.24 (d, 1H), 9.25 (s, 1H), 10.10 (s, 1H) and 13.72 (s, 1H). Anal. calcd for C14H11N3O2: C, 66.40; H, 4.38; N, 16.59. Found: C, 66.15; H, 4.20; N, 16.82.

Workup

  1. customThe product was purified by flash chromatography, on silica gel
  2. washeluted with 5 to 10% methanol in DCM
  3. customto give the product as an off white solid, 2.6 g (60% for 2 steps)

Sources & evidence

ORD record
ord-597ce7eaee6f4e9896a90d658f703f7f
Source dataset
uspto-grants-2010_05
Patent number
US07718692B2

Reaction notes

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