4-Amino-1-Boc-piperidine → HCID 178479359, compound

HRID 1881717Notes

Reaction equation

HRID 1881717 reaction equation
I.[NH2:2][C:3]1[C:4]([C:11]([NH:13][C:14](=[NH:17])SC)=[O:12])=[N:5][C:6]([Cl:10])=[C:7]([NH2:9])[N:8]=1.[NH2:18][CH:19]1[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]1>CN(C=O)C.O>[ClH:10].[NH2:2][C:3]1[C:4]([C:11]([NH:13][C:14](=[NH:17])[NH:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[O:12])=[N:5][C:6]([Cl:10])=[C:7]([NH2:9])[N:8]=1

Participants

5

Reactant 2

HCID 12682914-Amino-1-Boc-piperidineHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

Product 1

HCID 178479359HCID 178479359, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-2-methyl-isothiourea hydroiodide (7.2 g, 18.4 mmol) and 4-amino-1-Boc-piperidine (5.5 g, 27.5 mmol) in DMF (40 mL) is stirred and heated at 50° C. for 4 hours. The mixture is diluted with water (150 mL) and sonicated for 2 hours. The resulting suspension is collected by filtration and suspended in 4 M HCl in dioxane (40 mL). MeOH (20 mL) is added and the mixture is stirred at room temperature overnight and then filtered. The solid is washed with EtOH (2×10 mL) and dried to afford the title compound. [M+H]+ 313

Workup

  1. customsonicated for 2 hours
  2. filtrationThe resulting suspension is collected by filtration
  3. additionMeOH (20 mL) is added
  4. filtrationfiltered
  5. washThe solid is washed with EtOH (2×10 mL)
  6. customdried

Sources & evidence

ORD record
ord-7a3dfe5b6d9240a29d085dbdf46e1cc9
Source dataset
uspto-grants-2012_11
Patent number
US08318935B2

Reaction notes

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