Triethylsilane → N-(3-hydroxy-3-(hydroxy(phenyl)methyl)cyclohexyl)-3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamide

HRID 530861Notes

Reaction equation

HRID 530861 reaction equation
[C:1]([C:9]1([OH:53])[CH2:14][CH2:13][CH2:12][CH:11]([NH:15][C:16]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[N:23](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:22]=[C:21]3[C:46]2[CH:51]=[CH:50][N:49]=[C:48]([CH3:52])[CH:47]=2)=[O:17])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SiH](CC)(CC)CC>>[OH:53][C:9]1([CH:1]([OH:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:14][CH2:13][CH2:12][CH:11]([NH:15][C:16]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[NH:23][N:22]=[C:21]3[C:46]2[CH:51]=[CH:50][N:49]=[C:48]([CH3:52])[CH:47]=2)=[O:17])[CH2:10]1

Participants

3

Reactant 2

HCID 12052TriethylsilaneHCID 67985165N-(3-benzoyl-3-hydroxycyclohexyl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

Product 1

HCID 57410537N-(3-hydroxy-3-(hydroxy(phenyl)methyl)cyclohexyl)-3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamide

Procedure

N-(3-Benzoyl-3-hydroxycyclohexyl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide was stirred in neat TPA at room temperature for 10 minutes, and then Et3SiH (5 equiv.) was added. The reaction mixture was stirred at room temperature for 5 minutes, and then concentrated. The product was obtained after purification by reverse phase HPLC.

Workup

  1. concentrationconcentrated
  2. customThe product was obtained
  3. customafter purification by reverse phase HPLC

Sources & evidence

ORD record
ord-dd5a8423c0a44a858154c5c26c799326
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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