Methanol → 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(2-fluoro-5-{[(2,2,2-trifluoroethyl)amino]methyl}phenyl)-1H-indole-7-carboxamide trifluoroacetate

HRID 1806254Notes

Reaction equation

HRID 1806254 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:30]([NH2:32])=[O:31])[CH:17]=[C:18]([C:21]4[CH:26]=[C:25]([CH:27]=O)[CH:24]=[CH:23][C:22]=4[F:29])[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[F:33][C:34]([F:38])([F:37])[CH2:35][NH2:36].[CH3:39][OH:40]>ClCCl.C(O)(=O)C>[F:33][C:34]([F:38])([F:37])[C:39]([OH:4])=[O:40].[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:30]([NH2:32])=[O:31])[CH:17]=[C:18]([C:21]4[CH:26]=[C:25]([CH2:27][NH:36][CH2:35][C:34]([F:38])([F:37])[F:33])[CH:24]=[CH:23][C:22]=4[F:29])[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 866310203-[1-(ethylsulfonyl)-4-piperidinyl]-5-(2-fluoro-5-formylphenyl)-1H-indole-7-carboxamide

Product 1

HCID 866310213-[1-(ethylsulfonyl)-4-piperidinyl]-5-(2-fluoro-5-{[(2,2,2-trifluoroethyl)amino]methyl}phenyl)-1H-indole-7-carboxamide trifluoroacetateYield 24%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(2-fluoro-5-formylphenyl)-1H-indole-7-carboxamide (20 mg, 0.04 mmol) in dichloromethane (4 mL) and methanol (2 mL) was added 2 drops of acetic acid and 2,2,2-trifluoroethanamine (23 μL, 0.26 mmol). The resulting mixture was stirred overnight. All solvent was evaporated and dissolved in dimethyl sulfoxide (1 mL). Purified by Gilson Preparatory HPLC to give 5.2 mg of the title compound (24.0%).

Workup

  1. customAll solvent was evaporated
  2. dissolutiondissolved in dimethyl sulfoxide (1 mL)
  3. customPurified by Gilson Preparatory HPLC

Sources & evidence

ORD record
ord-da7a9516bc734bdd96a7b81946ad96b1
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

Loading…