Triethylsilane → N-(3-(2-fluorobenzyl)-3-hydroxycyclohexyl)-3-(2-methylpyridin-4-yl)4H-indazole-5-carboxamide

HRID 530842Notes

Reaction equation

HRID 530842 reaction equation
[F:1][C:2]1[CH:53]=[CH:52][CH:51]=[CH:50][C:3]=1[CH2:4][C:5]1([OH:49])[CH2:10][CH2:9][CH2:8][CH:7]([NH:11][C:12]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:18]=[C:17]3[C:42]2[CH:47]=[CH:46][N:45]=[C:44]([CH3:48])[CH:43]=2)=[O:13])[CH2:6]1.[SiH](CC)(CC)CC>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:53]=[CH:52][CH:51]=[CH:50][C:3]=1[CH2:4][C:5]1([OH:49])[CH2:10][CH2:9][CH2:8][CH:7]([NH:11][C:12]([C:14]2[CH2:15][C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]=[N:18][C:17]=3[C:42]2[CH:47]=[CH:46][N:45]=[C:44]([CH3:48])[CH:43]=2)=[O:13])[CH2:6]1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 67985157N-(3-(2-fluorobenzyl)-3-hydroxycyclohexyl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

Product 1

HCID 86698238N-(3-(2-fluorobenzyl)-3-hydroxycyclohexyl)-3-(2-methylpyridin-4-yl)4H-indazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-(3-(2-fluorobenzyl)-3-hydroxycyclohexyl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide was stirred in neat TFA 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 titled compound was obtained and purified by reverse phase HPLC.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-f26049ae674348768d9180de67905009
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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