Hydrochloric Acid → HCID 136173247, compound

HRID 629047Notes

Reaction equation

HRID 629047 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].N12CCCN=C1CCCCC2.[CH2:24]([O:26][C:27]1[CH:28]=[N:29][C:30]([N:33]2[C:38](=[O:39])[C:37]([CH2:40][C:41]3[CH:42]=[CH:43][C:44]([C:47]4[CH:56]=[CH:55][CH:54]=[CH:53][C:48]=4[C:49](=[N:51][OH:52])[NH2:50])=[N:45][CH:46]=3)=[C:36]([CH2:57][CH2:58][CH3:59])[N:35]=[C:34]2[CH:60]([CH3:62])[CH3:61])=[N:31][CH:32]=1)[CH3:25].Cl>O1CCCC1.ClCCl>[CH2:24]([O:26][C:27]1[CH:28]=[N:29][C:30]([N:33]2[C:38](=[O:39])[C:37]([CH2:40][C:41]3[CH:42]=[CH:43][C:44]([C:47]4[CH:56]=[CH:55][CH:54]=[CH:53][C:48]=4[C:49]4[NH:50][C:1](=[O:2])[O:52][N:51]=4)=[N:45][CH:46]=3)=[C:36]([CH2:57][CH2:58][CH3:59])[N:35]=[C:34]2[CH:60]([CH3:62])[CH3:61])=[N:31][CH:32]=1)[CH3:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 136338084HCID 136338084, compound

Product 1

HCID 136173247HCID 136173247, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Process 6: 1,1′-Carbonyldiimidazole (130 mg, 0.80 mmol) and 1,8-diazabicyclo[5.4.0]undeca-7-ene (122 mg, 0.80 mmol) were added to dichloromethane (4 mL) and tetrahydrofuran (4 mL) mixture solution of 2-{5-{[1-(5-ethoxypyrimidin-2-yl)-2-isopropyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}pyridin-2-yl}-N′-hydroxybenzimidamide (212 mg, 0.40 mmol) and stirred for 3 hours at room temperature. Once the reaction is completed, 1 M hydrochloric acid solution was added to the reaction mixture, which was then extracted with chloroform. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residues were subjected to silica gel column chromatography (chloroform/methanol=20:1) to give 3-{2-{5-{[1-(5-ethoxypyrimidin-2-yl)-2-isopropyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}pyridin-2-yl}phenyl}-1,2,4-oxadiazol-5(4H)-one (201 mg, 91%) as white amorphous.

Workup

  1. extractionwas then extracted with chloroform
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02e378dca74d497f8e7fd9f56767671b
Source dataset
uspto-grants-2016_04
Patent number
US09315493B2

Reaction notes

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