Tetrahydrofuran → HCID 178457908, compound

HRID 408644Notes

Reaction equation

HRID 408644 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([NH:12][C:13]([NH:15][CH2:16][C:17]2([CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[NH:14])=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.C1CCN2[C:34](=[N:35][CH2:36]CC2)[CH2:33][CH2:32]1.C1C[O:45]CC1>>[CH2:34]([NH:35][C:36]([N:20]1[CH2:19][CH2:18][C:17]([CH2:16][NH:15][C:13]([NH2:14])=[N:12][C:10]([C:3]2[C:2]([NH2:1])=[N:7][C:6]([NH2:8])=[C:5]([Cl:9])[N:4]=2)=[O:11])([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:22][CH2:21]1)=[O:45])[CH2:33][CH3:32]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178512090HCID 178512090, compound

Product 1

HCID 178457908HCID 178457908, compound

Procedure

To a mixture of 100 mg (0.198 mmol) N-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-N′-(4-phenethyl-piperidin-4-ylmethyl)-guanidine (example 2) and 29 μl DBU in 5 ml THF 12 μM (0.2 mmol) N-propylisocyanat is dropwise added and stirred at room temperature for 2 h. Then the mixture is concentrated under reduced pressure. The residue is purified via preparative reverse phase HPLC (gradient of acetonitrile and water+0.2% trifluoroacetic acid, 25° C.). Fractions containing the title compound were concentrated under reduced pressure.

Workup

  1. additionis dropwise added
  2. concentrationThen the mixture is concentrated under reduced pressure
  3. customThe residue is purified via preparative reverse phase HPLC (gradient of acetonitrile and water+0.2% trifluoroacetic acid, 25° C.)
  4. additionFractions containing the title compound
  5. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-296a3d96f6e441c19af7cf9361ab749a
Source dataset
uspto-grants-2014_06
Patent number
US08759349B2

Reaction notes

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