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

HRID 562066Notes

Reaction equation

HRID 562066 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-279c6e0c2b7e42d2acd4e330dcb525f3
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

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