1,1'-Carbonyldiimidazole → HCID 178496361, compound

HRID 1021320Notes

Reaction equation

HRID 1021320 reaction equation
C1N=CN([C:6]([N:8]2[CH:12]=[N:11]C=C2)=[O:7])C=1.[OH:13][CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:22]=[N:23][C:24]([N:27]3[CH2:32][CH2:31][N:30]([C:33](=[O:37])[CH2:34][O:35][CH3:36])[CH2:29][CH2:28]3)=[N:25][CH:26]=2)[CH:18]=[CH:19][CH:20]=1.C(=O)(O)O.[NH2:42]C(N)=N.[C:46]([OH:55])(=[O:54])[C@@H:47]([C@H:49]([C:51]([OH:53])=[O:52])[OH:50])[OH:48]>CC#N.O.CN(C=O)C>[C:51]([C@@H:49]([C@H:47]([C:46]([OH:55])=[O:54])[OH:48])[OH:50])([OH:53])=[O:52].[C:12]([NH:8][C:6](=[O:7])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[CH:22]=[N:23][C:24]([N:27]3[CH2:32][CH2:31][N:30]([C:33](=[O:37])[CH2:34][O:35][CH3:36])[CH2:29][CH2:28]3)=[N:25][CH:26]=2)[CH:16]=1)(=[NH:11])[NH2:42]

Participants

8

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 286947Carbonic acid-guanidine (1:1)HCID 444305L-Tartaric acidHCID 68309839HCID 68309839, compound

Product 1

HCID 178496361HCID 178496361, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent2×

Procedure

CDI (225 mg) was added to a mixture of 1-(4-{5-[3-(hydroxymethyl)phenyl]pyrimidin-2-yl}piperazin-1-yl)-2-methoxyethanone (216 mg) and DMF (6 ml), followed by stirring at room temperature for 2 hours. Then, guanidine carbonate (220 mg) was added to the mixture, followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction with CHCl3. The organic layer was dried over Na2SO4 and evaporated under reduced pressure. A mixture obtained by dissolving L-tartaric acid (59 mg) in a mixed solvent (1 ml) of MeCN and water at 9:1 was added to a mixture of the obtained residue (166.9 mg) in a mixed solvent (4 ml) of MeCN and water at 9:1, followed by stirring at room temperature. The precipitated solid was collected by filtration to obtain 3-{2-[4-(methoxy acetyl)piperazin-1-yl]pyrimidin-5-yl}benzyl carbamimidoylcarbamate L-tartrate (177 mg) as a colorless solid.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. extractionfollowed by extraction with CHCl3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated under reduced pressure
  5. customA mixture obtained
  6. stirringby stirring at room temperature
  7. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-47b06ba266dd4837bbdf6aac872f9548
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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