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HCID 178502137, compound → HCID 178484172, compound

HRID 451901
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Reaction equation

HRID 451901 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[N:43][C:44]#[N:45])[NH:24][C@H:25]([CH2:33][N:34](C)[C:35](OC(C)(C)C)=O)[CH2:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:18]2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[N:43][C:44]#[N:45])[NH:24][C@H:25]([CH2:33][NH:34][CH3:35])[CH2:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:18]2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 178502137HCID 178502137, compound

Product 1

HCID 178484172HCID 178484172, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

The methyl 2-((R)-(3-chlorophenyl)((R)-1-(N′-cyano-N—((S)-1-cyclohexyl-3-(N-methyl-N-(tert-butoxycarbonyl)amino)propan-2-yl)carbamimidoyl)piperidin-3-yl)methoxy)ethylcarbamate (8 mg, 0.0124 mmol) was dissolved in a solution of 4 N HCl/dioxane (5 mL). The reaction mixture was stirred at rt for 1 h and then concentrated in vacuo. The residue was purified by preparative HPLC to afford the product (4 mg, 59%).

Workup

  • concentrationconcentrated in vacuo
  • customThe residue was purified by preparative HPLC
  • Sources & evidence

    ORD record
    ord-dda18b5b14344cf2aa702d64c4752b33
    Source dataset
    uspto-grants-2013_07
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US08487108B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes