Hydrochloric Acid → N-[(3'-{[(3S)-3,4-dimethyl-1-piperazinyl]methyl}-6-fluoro-3-biphenylyl)methyl]-3-(4-piperidinylmethyl)benzamide

HRID 2080326Notes

Reaction equation

HRID 2080326 reaction equation
[CH3:1][C@@H:2]1[N:7]([CH3:8])[CH2:6][CH2:5][N:4]([CH2:9][C:10]2[CH:11]=[C:12]([C:16]3[C:21]([F:22])=[CH:20][CH:19]=[C:18]([CH2:23][NH:24][C:25]([C:27]4[CH:28]=[C:29]([CH2:33][CH:34]5[CH2:39][CH2:38][N:37](C(OC(C)(C)C)=O)[CH2:36][CH2:35]5)[CH:30]=[CH:31][CH:32]=4)=[O:26])[CH:17]=3)[CH:13]=[CH:14][CH:15]=2)[CH2:3]1.Cl>O1CCOCC1>[CH3:1][C@@H:2]1[N:7]([CH3:8])[CH2:6][CH2:5][N:4]([CH2:9][C:10]2[CH:11]=[C:12]([C:16]3[C:21]([F:22])=[CH:20][CH:19]=[C:18]([CH2:23][NH:24][C:25](=[O:26])[C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][CH:34]5[CH2:35][CH2:36][NH:37][CH2:38][CH2:39]5)[CH:28]=4)[CH:17]=3)[CH:13]=[CH:14][CH:15]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 577304331,1-dimethylethyl 4-{[3-({[(3'-{[(3S)-3,4-dimethyl-1-piperazinyl]methyl}-6-fluoro-3-biphenylyl)methyl]amino}carbonyl)phenyl]methyl)-1-piperidinecarboxylate

Product 1

HCID 11706395N-[(3'-{[(3S)-3,4-dimethyl-1-piperazinyl]methyl}-6-fluoro-3-biphenylyl)methyl]-3-(4-piperidinylmethyl)benzamideYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-{[3-({[(3′-{[(3S)-3,4-dimethyl-1-piperazinyl]methyl}-6-fluoro-3-biphenylyl)methyl]amino}carbonyl)phenyl]methyl)-1-piperidinecarboxylate (250 mg, 0.40 mmol) in 5 mL of 1,4-dioxane was added 4M HCl in 1,4-diozane (5 mL). The mixture was stirred at room temperature for 30 min. After removal of the solvent, the crude was purified by Gilson reverse phase HPLC, eluting with acetonitrile/water/0.1% TFA (10/90 to 70/30, v/v, over 12 min), to give the title compound (200 mg, 95%). LC/MS: m/z, 529 (M+H), 1.27 min.

Workup

  1. customAfter removal of the solvent
  2. customthe crude was purified by Gilson reverse phase HPLC
  3. washeluting with acetonitrile/water/0.1% TFA (10/90 to 70/30, v/v, over 12 min)

Sources & evidence

ORD record
ord-00ad17ceb1c24669817e731ed9c3baef
Source dataset
uspto-grants-2011_04
Patent number
US07932247B2

Reaction notes

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