Methyl ({2-[(tert-butoxycarbonyl)(7-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)amino]ethyl}amino)acetate → 5,6,7,8-Tetrahydro-7-(2-oxo-1-piperazinyl)-2-naphthalenecarbonitrile

HRID 1466055Notes

Reaction equation

HRID 1466055 reaction equation
C(OC([N:8]([CH:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][C:21]([C:27]#[N:28])=[CH:22][CH:23]=2)[CH2:18]1)[CH2:9][CH2:10][NH:11][CH2:12][C:13](OC)=[O:14])=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[O:14]=[C:13]1[CH2:12][NH:11][CH2:10][CH2:9][N:8]1[CH:17]1[CH2:18][C:19]2[CH:20]=[C:21]([C:27]#[N:28])[CH:22]=[CH:23][C:24]=2[CH2:25][CH2:26]1

Participants

4

Reactant 1

HCID 131732681Methyl ({2-[(tert-butoxycarbonyl)(7-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)amino]ethyl}amino)acetate

Product 1

HCID 895251235,6,7,8-Tetrahydro-7-(2-oxo-1-piperazinyl)-2-naphthalenecarbonitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of Methyl ({2-[(tert-butoxycarbonyl)(7-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)amino]ethyl}amino)acetate (145 mg, 0.37 mmol) in 15 mL of anhydrous DCM and 5 mL of TFA was stirred at room temperature for 2-3 hours. The reaction was concentrated. The residue was used directly in the next step. The residue was dissolved in 10 mL of EtOH, and was treated with TEA (5 mL). The mixture was heated to reflux overnight. The reaction was concentrated. The crude material was adsorbed onto silica gel and purified by MPLC (DCM:MeOH) to afford the title compound. MS m/z: 256 [M+1]+.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionThe residue was dissolved in 10 mL of EtOH
  3. additionwas treated with TEA (5 mL)
  4. temperatureThe mixture was heated
  5. temperatureto reflux overnight
  6. concentrationThe reaction was concentrated
  7. custompurified by MPLC (DCM:MeOH)

Sources & evidence

ORD record
ord-236f23eeaec747d7906d5d90af77a7ce
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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