Phosphorus oxychloride → HCID 58305987, compound

HRID 2088687Notes

Reaction equation

HRID 2088687 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([O:8][C:9](=[O:35])[CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[N:25]=[C:24]3[N:19]([C:20](=O)[NH:21][C:22]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=4[Cl:33])=[CH:23]3)[N:18]=2)[CH2:13][CH2:12]1)[CH3:7]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH2:6]([O:8][C:9](=[O:35])[CH2:10][N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[N:25]=[C:24]3[N:19]([C:20]([Cl:3])=[N:21][C:22]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=4[Cl:33])=[CH:23]3)[N:18]=2)[CH2:15][CH2:16]1)[CH3:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136104186Ethyl {4-[7-(2,4-dichlorophenyl)-5-oxo-5,6-dihydro[1,2,4]triazolo[1,5-c]pyrimidin-2-yl]piperidin-1-yl}acetate

Product 1

HCID 58305987HCID 58305987, compound

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Conditions

Temperature
120 °C

Procedure

5 ml of phosphoryl chloride were added to 500 mg (1.11 mmol) of ethyl{4-[7-(2,4-dichlorophenyl)-5-oxo-5,6-dihydro [1,2,4]triazolo[1,5-c]-pyrimidin-2-yl]piperidin-1-yl}acetate (Example 54A), 1.01 g (4.44 mmol) of benzyltriethylammonium chloride were added and the reaction mixture was stirred at 120° C. for 2.5 h. The reaction mixture was concentrated and carefully, with vigorous stirring, added to saturated aqueous sodium bicarbonate solution. The pH was adjusted to pH=7 by addition of solid sodium bicarbonate. The aqueous phase was extracted three times with dichloromethane. The combined organic phases were washed once with water, dried with magnesium sulfate and then freed from the solvent. Without further purification, this gave 506 mg (88% of theory) of the product.

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated
  3. additioncarefully, with vigorous stirring, added to saturated aqueous sodium bicarbonate solution
  4. additionThe pH was adjusted to pH=7 by addition of solid sodium bicarbonate
  5. extractionThe aqueous phase was extracted three times with dichloromethane
  6. washThe combined organic phases were washed once with water
  7. dry with materialdried with magnesium sulfate
  8. customWithout further purification

Sources & evidence

ORD record
ord-ffdb0c00752c4fbeb20f7d1f543016be
Source dataset
uspto-grants-2013_05
Patent number
US08436003B2

Reaction notes

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