Triethylamine → HCID 178474430, compound

HRID 1025518Notes

Reaction equation

HRID 1025518 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.P(Cl)(Cl)(Cl)=O.[C:11]([NH:14][C:15]1[NH:16][C:17](=O)[C:18]2[N:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:22]=[CH:21][C:19]=2[N:20]=1)(=[O:13])[CH3:12].C(N(CC)CC)C>C(#N)C>[C:11]([NH:14][C:15]1[N:16]=[C:17]([C:5]2[N:4]=[CH:3][NH:2][N:1]=2)[C:18]2[N:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:22]=[CH:21][C:19]=2[N:20]=1)(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 1360008912-acetamido-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 178474430HCID 178474430, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
50 °C

Procedure

A suspension of 1,2,4-triazole (120 mmol) and phosphorus oxychloride (36 mmol) in dry acetonitrile (150 ml) was added to a stirred suspension of the 2-acetamido-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidin-4(3H)-one of example 1 (12 mmol) and triethylamine (36 mmol) in dry acetonitrile (150 ml). The mixture was stirred at room temperature under nitrogen for 70 hours (or, alternatively, at 50° C. for 24 hours) and the yellow precipitate formed was filtered off, then successively washed with ethanol and ether, and further dried over P2O5 under vacuum. Solvents were evaporated in vacuo, then the crude residue was dissolved in dichloromethane and extracted with a diluted hydrochloric acid solution (HCl 0.01 N). The combined organic layers were dried over anhydrous MgSO4 and evaporated, thus providing the crude title compound in 72% yield, which was characterized by its mass spectrum as follows: MS (m/z): 350 ([M+H]+, 100).

Workup

  1. customformed
  2. filtrationwas filtered off
  3. washsuccessively washed with ethanol and ether
  4. dry with materialfurther dried over P2O5 under vacuum
  5. customSolvents were evaporated in vacuo
  6. dissolutionthe crude residue was dissolved in dichloromethane
  7. extractionextracted with a diluted hydrochloric acid solution (HCl 0.01 N)
  8. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  9. customevaporated

Sources & evidence

ORD record
ord-bcddb51e4d1c4cd585429b91bce34ab0
Source dataset
uspto-grants-2014_05
Patent number
US08729089B2

Reaction notes

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