(S)-(+)-2-(Aminomethyl)pyrrolidine → HCID 178508759, compound

HRID 2365475Notes

Reaction equation

HRID 2365475 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([NH:12][C:13](=[NH:16])SC)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.[NH2:17][CH2:18][C@@H:19]1[CH2:23][CH2:22][CH2:21]N1>CC(O)C>[NH2:1][C:2]1[C:3]([C:10]([N:12]=[C:13]2[N:16]3[CH2:21][CH2:22][CH2:23][CH:19]3[CH2:18][NH:17]2)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1

Participants

4

Reactant 2

HCID 2734054(S)-(+)-2-(Aminomethyl)pyrrolidineHCID 1404443183,5-Diamino-6-chloro-N-[(methylsulfanyl)methanimidoyl]pyrazine-2-carboxamide2×

Product 1

HCID 178508759HCID 178508759, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

1-(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-2-methyl-isothiourea (Intermediate A) (195 mg, 0.5 mmol) is suspended in propan-2-ol (10 ml) and (S)-2-(aminomethyl)pyrrolidine (100 mg, 1 mmol) is added. The mixture is heated at 60° C. for 18 hours, allowed to cool to room temperature and the precipitate is removed by filtration. The filtrate is concentrated in vacuo and the residue purified by chromatography (SiO2, DCM/MeOH) to afford the title compound as a light, yellow gum; [M+H]+ 296

Workup

  1. temperatureto cool to room temperature
  2. customthe precipitate is removed by filtration
  3. concentrationThe filtrate is concentrated in vacuo
  4. customthe residue purified by chromatography (SiO2, DCM/MeOH)

Sources & evidence

ORD record
ord-b7617457456241d2b5be530632f89ba3
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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