1,1'-Carbonyldiimidazole → HCID 86656657, compound

HRID 882917Notes

Reaction equation

HRID 882917 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([OH:12])=O)=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[C:25]([O:29][C:30](=[O:36])[N:31]([CH2:33][CH2:34][NH2:35])[CH3:32])([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C>[C:25]([O:29][C:30](=[O:36])[N:31]([CH2:33][CH2:34][NH:35][C:10]([C:3]1[C:2]([NH2:1])=[N:7][C:6]([NH2:8])=[C:5]([Cl:9])[N:4]=1)=[O:12])[CH3:32])([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 2756424N-Boc-N-methylethylenediamineHCID 64521193,5-Diamino-6-chloro-pyrazine acid

Product 1

HCID 86656657HCID 86656657, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid (3.85 g, 20.5 mmol) in DMF (90 mL) is treated with CDI (6.64 g, 41 mmol) and stirred at RT for 1 h. To this mixture is added N-(2-aminoethyl)-N-methyl carbamic acid tert-butyl ester (5.0 g, 28.6 mmol) and stirring continues at RT for 72 h. The solvent is removed in vacuo and the residue is partitioned between EtOAc (100 mL) and water (60 mL). The organic portion is separated, dried (MgSO4) and concentrated in vacuo. The resulting yellow residue is washed with diethyl ether to afford the title compound which is used in the next step without further purification. [M+H]+ 345.

Workup

  1. stirringstirring
  2. waitcontinues at RT for 72 h
  3. customThe solvent is removed in vacuo
  4. customthe residue is partitioned between EtOAc (100 mL) and water (60 mL)
  5. customThe organic portion is separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. washThe resulting yellow residue is washed with diethyl ether

Sources & evidence

ORD record
ord-f408b040528b4845b3a622dc60d103b4
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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