1-Aminocyclopentanemethanamine → HCID 178508758, compound
Reaction equation
[NH2:1][CH2:2][C:3]1([NH2:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.[NH2:9][C:10]1[C:11]([C:18]([NH:20][C:21](=N)SC)=[O:19])=[N:12][C:13]([Cl:17])=[C:14]([NH2:16])[N:15]=1>CC(O)C>[NH:8]1[C:3]2([CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:2][NH:1]/[C:21]/1=[N:20]/[C:18]([C:11]1[C:10]([NH2:9])=[N:15][C:14]([NH2:16])=[C:13]([Cl:17])[N:12]=1)=[O:19]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A solution of crude 1-aminomethyl-cyclopentylamine (Intermediate J) (80 mg, 0.70 mmol) in propan-2-ol (1.0 ml) is added to a suspension of 1-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-2-methyl-isothiourea (Intermediate A) (208 mg, 0.54 mmol) in propan-2-ol (1.08 ml) and heated at 70° C. for 2 days. After cooling to room temperature, the reaction mixture is filtered under vacuum, and the solid is rinsed with MeOH. The filtrate is concentrated in vacuo to afford a bright yellow residue which is loaded onto a SCX-2 cartridge and eluted with 33% NH3 (4 drops) in MeOH (5 ml×2). The methanolic ammonia fractions are combined and concentrated in vacuo. Purification using mass directed preparative LCMS eluting with 95% Water+0.1% NH3: 5% Acetonitrile to affords the title compound; [M+H]+ 310.
Workup
- temperatureAfter cooling to room temperature
- filtrationthe reaction mixture is filtered under vacuum
- washthe solid is rinsed with MeOH
- concentrationThe filtrate is concentrated in vacuo
- customto afford a bright yellow residue which
- washeluted with 33% NH3 (4 drops) in MeOH (5 ml×2)
- concentrationconcentrated in vacuo
- customPurification
- washeluting with 95% Water+0.1% NH3
Sources & evidence
- ORD record
- ord-cfd2f679d41b458daae86ce106bee25f
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08039472B2
Reaction notes
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