Dimethylformamide → HCID 136059242, compound

HRID 1622979Notes

Reaction equation

HRID 1622979 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]undeca-7-ene (460 mg, 3.02 mmol) were added to a dimethylformamide (25 mL) solution 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 the reaction solution was stirred at room temperature for 3 hours. After completion of the reaction, the reaction solution 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 residues obtained were purified by silica gel column chromatography (ethyl acetate), to obtain 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%, 2-step yield) as a pale yellow oil.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residues obtained
  7. customwere purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-6b58041af3624377bb33bef02a4cfbf6
Source dataset
uspto-grants-2014_07
Patent number
US08778954B2

Reaction notes

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