Trifluoroacetic acid methylene chloride → HCID 117992447, compound

HRID 717094Notes

Reaction equation

HRID 717094 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:35])[C:15](=[O:34])[C:16]2[CH:21]=[CH:20][C:19]([C:22]3[NH:23][C:24](=[O:33])[C:25]4[C:30]([CH:31]=3)=[C:29]([CH3:32])[CH:28]=[CH:27][CH:26]=4)=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>>[CH3:35][N:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[C:15](=[O:34])[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[NH:23][C:24](=[O:33])[C:25]3[C:30]([CH:31]=2)=[C:29]([CH3:32])[CH:28]=[CH:27][CH:26]=3)=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 117992919HCID 117992919, compound

Product 1

HCID 117992447HCID 117992447, compoundYield 14.5%

Procedure

To 4-{methyl-[4-(5-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzoyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (21 mg, 0.044 mmol) was added 2:1 CH2Cl2/TFA (1 mL) and the reaction mixture stirred at RT for 1 h. The solvent was removed in vacuo, re-dissolved in MeOH and passed through an SCX-2 cartridge (1 g). The column was washed with MeOH (4× column volumes), the desired product eluted from the cartridge with 0.5M NH3/MeOH (4× column volumes) and concentrated in vacuo. The crude product was purified by reverse phase preparative HPLC-MS to obtain N-methyl-4-(5-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-N-piperidin-4-yl-benzamide as a white solid (2.4 mg, 14%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionre-dissolved in MeOH
  3. washThe column was washed with MeOH (4× column volumes)
  4. washthe desired product eluted from the cartridge with 0.5M NH3/MeOH (4× column volumes)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by reverse phase preparative HPLC-MS

Sources & evidence

ORD record
ord-b124b9c39e174d1abd3cb9d37755d231
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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