Triethylsilane → N-(3-(2-fluorobenzyl)-3-methoxycyclohexyl)-3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamide

HRID 530848Notes

Reaction equation

HRID 530848 reaction equation
[F:1][C:2]1[CH:54]=[CH:53][CH:52]=[CH:51][C:3]=1[CH2:4][C:5]1([O:49][CH3:50])[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:54]=[CH:53][CH:52]=[CH:51][C:3]=1[CH2:4][C:5]1([O:49][CH3:50])[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)[NH: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 67984947N-(3-(2-fluorobenzyl)-3-methoxycyclohexyl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

Product 1

HCID 57410417N-(3-(2-fluorobenzyl)-3-methoxycyclohexyl)-3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-(3-(2-fluorobenzyl)-3-methoxycyclohexyl)-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 product was obtained and purified by reverse phase HPLC. Two diastereomers obtained.

Workup

  1. concentrationconcentrated
  2. customThe product was obtained
  3. custompurified by reverse phase HPLC
  4. customTwo diastereomers obtained

Sources & evidence

ORD record
ord-fa8ad612ab3840eebea1e3c22de9926c
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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