HCID 54034171, compound → HCID 17985229, compound

HRID 1432915Notes

Reaction equation

HRID 1432915 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24](=[NH:26])[NH2:25])=[CH:20][CH:19]=2)[C:13](=[O:27])[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>CO.CC(O)=O.[Pd]>[O:27]=[C:13]1[CH2:12][NH:11][CH2:16][CH2:15][N:14]1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([NH2:26])=[NH:25])=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 54034171HCID 54034171, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 17985229HCID 17985229, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 4-(4-carbamimidoylbenzyl)-3-oxopiperazine-1-carboxylic acid benzyl ester (2.0 g, 5.0 mmol) in 40 mL of MeOH and 4 mL of AcOH is added 10% Pd/C (0.4 g). The atmosphere above the reaction is replaced by hydrogen. After 4 hours, the solution is filtered through a pad of Celite. The organic layer is concentrated. The resulting crude product is purified by RP-HPLC eluting in a gradient of 10% CH3CN/H2O (0.1%TFA) to 40% CH3CN/H2O (0.1% TFA). The title compound is obtained as a white foam. 1H NMR (d6-DMSO, 300 MHz) δ9.3 (bs, 4H), 9.1 (bs, 2H), 7.83 (d, 2H), 7.42 (d, 2H), 4.78 (s, 2H), 3.80 (s, 2H), 3.44 (m, 2H), 3.32 (m, 2H).

Workup

  1. filtrationthe solution is filtered through a pad of Celite
  2. concentrationThe organic layer is concentrated
  3. customThe resulting crude product is purified by RP-HPLC
  4. washeluting in a gradient of 10% CH3CN/H2O (0.1%TFA) to 40% CH3CN/H2O (0.1% TFA)

Sources & evidence

ORD record
ord-0cfb78aa2f1744b0a37b04ed235fa45b
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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