Hydrochloric Acid → HCID 178508795, compound

HRID 1881712Notes

Reaction equation

HRID 1881712 reaction equation
[CH2:1]([O:8][C:9]([N:11]=[C:12]([NH:27][C:28]([C:30]1[C:35]([NH2:36])=[N:34][C:33]([NH2:37])=[C:32]([Cl:38])[N:31]=1)=[O:29])[NH:13][CH:14]1[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCOCC1.CO>[NH2:36][C:35]1[C:30]([C:28]([NH:27][C:12](=[N:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[NH:13][CH:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)=[O:29])=[N:31][C:32]([Cl:38])=[C:33]([NH2:37])[N:34]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178452100HCID 178452100, compound

Product 1

HCID 178508795HCID 178508795, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
40 °C

Procedure

A suspension of tert-butyl 4-(2-(benzyloxycarbonyl)-3-(3,5-diamino-6-chloropyrazine-2-carbonyl)guanidino)piperidine-1-carboxylate (Step 1) (6.3 g, 11.5 mmol) in dioxane (250 mL) and MeOH (small volume) is treated with 4 M HCl in dioxane (40 mL) and left to stir overnight at 40° C. The resulting suspension is filtered and the solid is partitioned between water (800 mL) and EtOAc (800 mL). 1 M NaOH is added to adjust the pH to pH 8 and the organic portion is separated, dried (MgSO4) and concentrated in vacuo to afford the title compound. [M+H]+ 447

Workup

  1. waitleft
  2. filtrationThe resulting suspension is filtered
  3. customthe solid is partitioned between water (800 mL) and EtOAc (800 mL)
  4. addition1 M NaOH is added
  5. customthe organic portion is separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b6dc531a276a4a138607479be9ee1a52
Source dataset
uspto-grants-2012_11
Patent number
US08318935B2

Reaction notes

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