Triethylamine → HCID 11648616, compound

HRID 1670791Notes

Reaction equation

HRID 1670791 reaction equation
C(N(CC)CC)C.Cl.[CH:9]1([CH2:12][NH2:13])[CH2:11][CH2:10]1.[Cl:14][C:15]1[C:16]([N:21]2[C:25]([C:26]3[O:31][C:30](=[O:32])[C:29]4[CH:33]=[CH:34][CH:35]=[C:36]([CH3:37])[C:28]=4[N:27]=3)=[CH:24][C:23]([C:38]([F:41])([F:40])[F:39])=[N:22]2)=[N:17][CH:18]=[CH:19][CH:20]=1>O1CCCC1>[CH:9]1([CH2:12][NH:13][C:30]([C:29]2[C:28]([NH:27][C:26]([C:25]3[N:21]([C:16]4[C:15]([Cl:14])=[CH:20][CH:19]=[CH:18][N:17]=4)[N:22]=[C:23]([C:38]([F:40])([F:39])[F:41])[CH:24]=3)=[O:31])=[C:36]([CH3:37])[CH:35]=[CH:34][CH:33]=2)=[O:32])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81671(Cyclopropylmethyl)ammonium chlorideHCID 231503482-[1-(3-chloro-2-pyridinyl)-3-trifluoromethyl-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazine-4-one

Product 1

HCID 11648616HCID 11648616, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.49 g of triethylamine was gradually dropwise added to a mixed solution comprising 0.8 g of cyclopropylmethylamine hydrochloride and 40 ml of tetrahydrofuran under cooling with ice, followed by stirring at room temperature for 30 minutes. Then, a mixed solution comprising 1 g of 2-[1-(3-chloro-2-pyridyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazin-4-one and 10 ml of tetrahydrofuran was gradually dropwise added. After completion of the dropwise addition, the mixed solution was reacted for 4 hours under reflux. After completion of the reaction, the solvent was distilled off under reduced pressure, and to the residue, ethyl acetate and water were added for extraction. The organic layer was washed with water and a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to obtain 0.54 g of the desired product having a melting point of 199.4° C.

Workup

  1. temperatureunder cooling with ice
  2. additionwas gradually dropwise added
  3. additionAfter completion of the dropwise addition
  4. customthe mixed solution was reacted for 4 hours
  5. temperatureunder reflux
  6. customAfter completion of the reaction
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionto the residue, ethyl acetate and water were added for extraction
  9. washThe organic layer was washed with water
  10. dry with materiala saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate
  11. distillationThe solvent was distilled off under reduced pressure
  12. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-fc8388e2d70d4253966f9dbec1afc769
Source dataset
uspto-grants-2011_08
Patent number
US07994201B2

Reaction notes

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