Triethylamine → HCID 11475967, compound

HRID 1168136Notes

Reaction equation

HRID 1168136 reaction equation
[NH2:1][C:2]1[C:3]([OH:23])=[C:4]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[N:12]([CH3:21])[C:11]2=[O:22])[C:5]([F:9])=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH:31]1([C:36](Cl)=O)[CH2:35][CH2:34][CH2:33][CH2:32]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[Cl:8][C:7]1[C:2]2[N:1]=[C:36]([CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[O:23][C:3]=2[C:4]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[N:12]([CH3:21])[C:11]2=[O:22])=[C:5]([F:9])[CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 78284Cyclopentanecarbonyl chlorideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 11279654HCID 11279654, compound2×

Product 1

HCID 11475967HCID 11475967, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
20 °C

Procedure

0.48 g of 3-[3-amino-4-chloro-6-fluoro-2-hydroxyphenyl]-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione (from intermediate 7) was initially charged with 0.14 g of triethylamine in 30 ml of absolute xylene, and the mixture was, at 0° C., admixed dropwise with 0.18 g of cyclopentanecarbonyl chloride. After 10 minutes, the mixture was warmed to 20° C., 0.1 g of pyridinium p-toluenesulfonate was added and the mixture was heated at reflux for six hours. After cooling, the xylene phase was washed three times with 30 ml of water each time, dried over sodium sulfate and freed from the solvent under reduced pressure. The crude product was purified by medium pressure liquid chromatography (MPLC); mobile phase: cyclohexane/ethyl acetate (9:1). Yield: 0.27 g;

Workup

  1. customwas, at 0° C.
  2. temperaturethe mixture was heated
  3. temperatureat reflux for six hours
  4. temperatureAfter cooling
  5. washthe xylene phase was washed three times with 30 ml of water each time
  6. dry with materialdried over sodium sulfate
  7. customThe crude product was purified by medium pressure liquid chromatography (MPLC)

Sources & evidence

ORD record
ord-4e8988f3a4654f09b70e6571c6e9b8be
Source dataset
uspto-grants-2003_09
Patent number
US06624119B1

Reaction notes

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