Guanidine → HCID 178482728, compound

HRID 1725159Notes

Reaction equation

HRID 1725159 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][CH:8]=[C:7]1[C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:33])[N:24]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH3:25])=[CH:19][CH:18]=1)C.[NH2:35][C:36]([NH2:38])=[NH:37]>CS(C)=O>[NH2:37][C:36]([NH:38][C:4](=[O:3])[CH2:5][N:6]1[C:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:9][CH:8]=[C:7]1[C:17]1[CH:22]=[CH:21][C:20]([C:23]([N:24]([CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH3:25])=[O:33])=[CH:19][CH:18]=1)=[NH:35]

Participants

4

Reactant 2

HCID 3520GuanidineHCID 57423670HCID 57423670, compound

Product 1

HCID 178482728HCID 178482728, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To the ester from step 6 (200 μmol) is disslved in DMSO (1 mL) and a solution of neutralized guanidine in DMSO is added (500 μL, 2 M in DMSO) and allowed to sit at room temperature for 16 h. The reaction is quenched by the addition of glacial AcOH (100 μL) and distilled water (200 μL) and concentrated in vacuo. The residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL total) and purified by Gilson preparative HPLC system.

Workup

  1. customThe reaction is quenched by the addition of glacial AcOH (100 μL)
  2. distillationdistilled water (200 μL)
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL total)
  5. custompurified by Gilson preparative HPLC system

Sources & evidence

ORD record
ord-c673846c17c049adb70cfeda2960f91d
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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