Trifluoroacetic acid → Trifluoroacetic acid

HRID 1467346Notes

Reaction equation

HRID 1467346 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]([NH2:18])=[O:17])[CH:14]=3)[N:9](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:8]=2)=[CH:3][CH:2]=1.C([SiH](CC)CC)C.[C:45]([OH:51])([C:47]([F:50])([F:49])[F:48])=[O:46]>CN(C=O)C>[C:45]([OH:51])([C:47]([F:50])([F:49])[F:48])=[O:46].[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]([NH2:18])=[O:17])[CH:14]=3)[NH:9][N:8]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86681287HCID 86681287, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 67996842HCID 67996842, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N—((R)-1-((S or R)-2-(Dimethylamino)-1-(2-fluorophenyl)-2-oxoethyl)piperidin-3-yl)-3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide (53 mg, 0.071 mmol) was stirred in TFA (0.5 mL) at room temperature for 30 minutes. triethylsilane (0.015 mL, 0.093 mmol) was added and the reaction mixture diluted with DMF (1 mL). The solution was purified by reverse-phase, mass-triggered prep-HPLC. The product fraction was lyophilized to give the bis TFA salt of N—((R)-1-((S or R)-2-(dimethylamino)-1-(2-fluorophenyl)-2-oxoethyl)piperidin-3-yl)-3-(pyridin-4-yl)-1H-indazole-5-carboxamide as a white solid.

Workup

  1. customThe solution was purified by reverse-phase, mass-triggered prep-HPLC

Sources & evidence

ORD record
ord-0e2a952a85444505b81abab61ac420e0
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

Loading…