Dimethylformamide → HCID 136059242, compound

HRID 629043Notes

Reaction equation

HRID 629043 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].N12CCCN=C1CCCCC2.CN(C)C=O.[CH2:29]([C:33]1[N:34]=[C:35]([CH3:63])[N:36]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][N:58]=2)[C:37](=[O:56])[C:38]=1[CH2:39][C:40]1[CH:41]=[CH:42][C:43]([C:46]2[CH:55]=[CH:54][CH:53]=[CH:52][C:47]=2[C:48](=[N:50][OH:51])[NH2:49])=[N:44][CH:45]=1)[CH2:30][CH2:31][CH3:32]>O>[CH2:29]([C:33]1[N:34]=[C:35]([CH3:63])[N:36]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][N:58]=2)[C:37](=[O:56])[C:38]=1[CH2:39][C:40]1[CH:41]=[CH:42][C:43]([C:46]2[CH:55]=[CH:54][CH:53]=[CH:52][C:47]=2[C:48]2[NH:49][C:1](=[O:2])[O:51][N:50]=2)=[N:44][CH:45]=1)[CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 136332407HCID 136332407, compound

Product 1

HCID 136059242HCID 136059242, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Process 3: 1,1′-Carbonyldiimidazole (490 mg, 3.02 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (460 mg, 3.02 mmol) were added to dimethylformamide solution (25 mL) of 2-{5-{[4-butyl-2-methyl-6-oxo-1-(pyridin-2-yl)-1,6-dihydropyrimidin-5-yl]methyl}pyridin-2-yl}-N′-hydroxybenzimidamide (430 mg, 0.918 mmol) and stirred for 3 hours at room temperature. Once the reaction is completed, the reaction mixture was added water and extracted with ethyl acetate. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residues were purified by silica gel column chromatography (ethyl acetate) to give 3-{2-{5-{[4-butyl-2-methyl-6-oxo-1-(pyridin-2-yl)-1,6-dihydropyrimidin-5-yl]methyl}pyridin-2-yl}phenyl}-1,2,4-oxadiazol-5(4H)-one (160 mg, 35%, two step yield) as weak yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residues were purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-a25b49206f374428b752164e9f2cc954
Source dataset
uspto-grants-2016_04
Patent number
US09315493B2

Reaction notes

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