Triethylsilane → N-(3-(3-fluorophenoxy)-3-(hydroxymethyl)cyclohexyl)-3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamide

HRID 530853Notes

Reaction equation

HRID 530853 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:52]=[CH:53][CH:54]=1)[O:5][C:6]1([CH2:50][OH:51])[CH2:11][CH2:10][CH2:9][CH:8]([NH:12][C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:19]=[C:18]3[C:43]2[CH:48]=[CH:47][N:46]=[C:45]([CH3:49])[CH:44]=2)=[O:14])[CH2:7]1.[SiH](CC)(CC)CC>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:52]=[CH:53][CH:54]=1)[O:5][C:6]1([CH2:50][OH:51])[CH2:11][CH2:10][CH2:9][CH:8]([NH:12][C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[C:18]3[C:43]2[CH:48]=[CH:47][N:46]=[C:45]([CH3:49])[CH:44]=2)=[O:14])[CH2:7]1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 67985826N-(3-(3-fluorophenoxy)-3-(hydroxymethyl)cyclohexyl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

Product 1

HCID 57410534N-(3-(3-fluorophenoxy)-3-(hydroxymethyl)cyclohexyl)-3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-(3-(3-fluorophenoxy)-3-(hydroxymethyl)cyclohexyl)-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 after purification by reverse phase HPLC. The diastereomers were separated and enantiomers were separated on chiral column (AD) on a HPLC.

Workup

  1. concentrationconcentrated
  2. customThe product was obtained
  3. customafter purification by reverse phase HPLC
  4. customThe diastereomers were separated
  5. customenantiomers were separated on chiral column (AD) on a HPLC

Sources & evidence

ORD record
ord-87e0f0ba5da9486bae9ef8b6eeef81b2
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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