(S)-3-Amino-1-benzylpiperidine → HCID 178512404, compound

HRID 77510Notes

Reaction equation

HRID 77510 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([NH:12][C:13](SC)=[NH:14])=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.[NH2:17][C@H:18]1[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:19]1>C1COCC1>[CH2:24]([N:20]1[CH2:21][CH2:22][CH2:23][C@H:18]([NH:17][C:13]([NH:12][C:10]([C:3]2[C:2]([NH2:1])=[N:7][C:6]([NH2:8])=[C:5]([Cl:9])[N:4]=2)=[O:11])=[NH:14])[CH2:19]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 854131(S)-3-Amino-1-benzylpiperidineHCID 1404443183,5-Diamino-6-chloro-N-[(methylsulfanyl)methanimidoyl]pyrazine-2-carboxamide2×

Product 1

HCID 178512404HCID 178512404, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 60 mg (0.27 mmol) 3,5-diamino-6-chloro-N[(methylsulfanyl)methanimidoyl]-pyrazine-2-carboxamide (intermediate 3) and 60 mg (S)-3-amino-1-benzyl-piperidine in 2 ml THF is stirred at 70° C. overnight. Then the reaction mixture is concentrated under reduced pressure and the residue is purified by preparative reverse phase HPLC (gradient of acetonitrile and water+0.2% trifluoroacetic acid, 25° C.). Fractions containing the title compound were concentrated under reduced pressure treated with excess HCl in methanol and evaporated again.

Workup

  1. concentrationThen the reaction mixture is concentrated under reduced pressure
  2. customthe residue is purified by preparative reverse phase HPLC (gradient of acetonitrile and water+0.2% trifluoroacetic acid, 25° C.)
  3. additionFractions containing the title compound
  4. concentrationwere concentrated under reduced pressure
  5. additiontreated with excess HCl in methanol
  6. customevaporated again

Sources & evidence

ORD record
ord-c6f0eea0b5af45dabed6e8aec7f3c8e9
Source dataset
uspto-grants-2014_09
Patent number
US08841309B2

Reaction notes

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