Sodium Bicarbonate → HCID 58305976, compound

HRID 2088680Notes

Reaction equation

[ClH:1].[CH:2]1([CH2:5][N:6]2[CH2:11][CH2:10][CH:9]([C:12]3[N:20]=[C:19]4[N:14]([C:15](=O)[NH:16][C:17]([C:21]5[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=5[Cl:28])=[CH:18]4)[N:13]=3)[CH2:8][CH2:7]2)[CH2:4][CH2:3]1.C(=O)(O)[O-].[Na+]>P(Cl)(Cl)(Cl)=O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:15]1[N:14]2[N:13]=[C:12]([CH:9]3[CH2:10][CH2:11][N:6]([CH2:5][CH:2]4[CH2:4][CH2:3]4)[CH2:7][CH2:8]3)[N:20]=[C:19]2[CH:18]=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[N:16]=1

Participants

Conditions

Temperature: 120 °C

Procedure

356 mg (0.85 mmol) of 2-[1-(cyclopropylmethyl)piperidin-4-yl]-7-(2,4-dichlorophenyl)[1,2,4]-triazolo[1,5-c]pyrimidin-5(6H)-one hydrochloride (Example 46A) were initially charged in phosphorus oxychloride (6 ml), 775 mg (3.40 mmol) of benzyltriethylammonium chloride were added and the mixture was stirred at 120° C. for 2.5 h. The reaction mixture was poured into saturated aqueous sodium bicarbonate solution (150 ml), and solid sodium bicarbonate was added until a pH of 7 had been reached. The mixture was extracted with dichloromethane (3×50 ml), and the combined organic phases were washed with water (50 ml), dried over magnesium sulfate and concentrated. This gave 307 mg (83% of theory) of the product as a solid.

Workup

additionwas added until a pH of 7
extractionThe mixture was extracted with dichloromethane (3×50 ml)
washthe combined organic phases were washed with water (50 ml)
dry with materialdried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-ddce0dd1f7954abd947554f6720ac734
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436003B2

Reaction notes

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