4-Amino-1-Boc-piperidine → HCID 178452100, compound

HRID 1881711Notes

Reaction equation

HRID 1881711 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([NH:12][C:13](=[N:16][C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)SC)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.[NH2:27][CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]1>C1COCC1>[CH2:19]([O:18][C:17]([N:16]=[C:13]([NH:12][C:10]([C:3]1[C:2]([NH2:1])=[N:7][C:6]([NH2:8])=[C:5]([Cl:9])[N:4]=1)=[O:11])[NH:27][CH:28]1[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:32][CH2:33]1)=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 12682914-Amino-1-Boc-piperidineHCID 72513286HCID 72513286, compound2×

Product 1

HCID 178452100HCID 178452100, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of benzyl (3,5-diamino-6-chloropyrazine-2-carboxamido)(methylthio)methylenecarbamate (Intermediate B) (6.7 g, 17 mmol) and 4-amino-1-Boc-piperidine (4.1 g, 20.4 mmol) in dry THF (150 mL) is heated at reflux overnight. The solvent is removed in vacuo and a solid forms on concentration. The solid is separated and retained and the remaining mother liquor is concentrated to form a solid. The solid is partitioned between EtOAc and water and the organic portion is dried (MgSO4) and part concentrated in vacuo and then left to crystallise. The crystals are filtered and combined with the retained solid to afford the title product. [M+H]+ 547

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. customThe solvent is removed in vacuo
  4. concentrationa solid forms on concentration
  5. customThe solid is separated
  6. concentrationthe remaining mother liquor is concentrated
  7. customto form a solid
  8. customThe solid is partitioned between EtOAc and water
  9. dry with materialthe organic portion is dried (MgSO4) and part
  10. concentrationconcentrated in vacuo
  11. waitleft
  12. customto crystallise
  13. filtrationThe crystals are filtered

Sources & evidence

ORD record
ord-2f17dbc80a594b1286ee2c5eef28b282
Source dataset
uspto-grants-2012_11
Patent number
US08318935B2

Reaction notes

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