Diethyl Ether → HCID 178508793, compound

HRID 1665113Notes

Reaction equation

HRID 1665113 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C@H:5]1[CH2:9][NH:8]/[C:7](=[N:10]\[C:11]([C:13]2[C:18]([NH2:19])=[N:17][C:16]([NH2:20])=[C:15]([Cl:21])[N:14]=2)=[O:12])/[NH:6]1.[C:22]([N:29]1[CH:33]=[CH:32]N=C1)(N1C=CN=C1)=[O:23].C(N)[C:35]1[CH:40]=[CH:39]C=[CH:37][CH:36]=1.C(OCC)C>CN(C=O)C.CO>[CH2:33]([NH:29][C:22](=[O:23])[NH:1][CH2:2][CH2:3][CH2:4][C@H:5]1[CH2:9][NH:8]/[C:7](=[N:10]\[C:11]([C:13]2[C:18]([NH2:19])=[N:17][C:16]([NH2:20])=[C:15]([Cl:21])[N:14]=2)=[O:12])/[NH:6]1)[C:32]1[CH:39]=[CH:40][CH:35]=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7504Benzylamine2×HCID 682631,1'-CarbonyldiimidazoleHCID 178511031HCID 178511031, compound

Product 1

HCID 178508793HCID 178508793, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid [(S)-4-(3-amino-propyl)-imidazolidin-(2E)-ylidene]-amide (Ex. 31) (0.040 g, 0.128 mmol) in DMF (2 ml) is added 1,1′-carbonyldiimidazole (0.023 g, 0.141 mmol) and the reaction mixture is stirred for 1 hour at room temperature. Benzylamine (0.014 ml, 0.128 mmol) is added and additional benzylamine (0.014 ml, 0.128 mmol) is added at hourly intervals for a total of 3 hours. Purification is by diluting the reaction with 2N NaOH (30 ml) and extracting the product into EtOAc (40 ml). The organic phase is washed with 2N NaOH (30 ml), dried over MgSO4 and the solvent evaporated in vacuo to yield a yellow oil. The oil is dissolved in methanol (0.75 ml) and diethyl ether (5 ml) added to triturate a yellow solid. This solid is filtered off and the filtrate formed a further precipitate. This yellow solid is collected by filtration and rinsed with diethyl ether to give the title compound; [M+H]+ 446.1

Workup

  1. customPurification
  2. additionby diluting
  3. customthe reaction with 2N NaOH (30 ml)
  4. extractionextracting the product into EtOAc (40 ml)
  5. washThe organic phase is washed with 2N NaOH (30 ml)
  6. dry with materialdried over MgSO4
  7. customthe solvent evaporated in vacuo
  8. customto yield a yellow oil
  9. customto triturate a yellow solid
  10. filtrationThis solid is filtered off
  11. customthe filtrate formed a further precipitate
  12. filtrationThis yellow solid is collected by filtration
  13. washrinsed with diethyl ether

Sources & evidence

ORD record
ord-d20d0e9687824815b05b4057299855c0
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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