Hydrochloric Acid → HCID 58467968, compound

HRID 2403564Notes

Reaction equation

HRID 2403564 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[CH:13]1([OH:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[H-].[Na+].[Cl-].[Na+].[CH3:24][S:25]([C:28]1[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26].Cl.C(=O)([O-])O.[Na+]>C(OCC)C.C(#N)C.O1CCOCC1>[CH:13]1([O:19][C:6]2[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=[C:2]([NH:34][C:31]3[CH:30]=[CH:29][C:28]([S:25]([CH3:24])(=[O:27])=[O:26])=[CH:33][CH:32]=3)[N:7]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 796174-(Methylsulfonyl)anilineHCID 516892Sodium BicarbonateHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidine

Product 1

HCID 58467968HCID 58467968, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.00 g (4.63 mmol) of 2,4-dichloro-5-trifluoromethylpyrimidine and 0.64 ml (5.99 mmol) of cyclohexanol in 12.2 ml of diethyl ether and 12.2 ml of acetonitrile was admixed at 0° C. with stirring in portions with 0.24 g of sodium hydride (55%). The mixture was slowly warmed to room temperature overnight in an ice bath. The mixture was admixed with ice and dilute sodium chloride solution. Extraction was carried out with ethyl acetate (2×). The combined organic phases were dried (Na2SO4), filtered and concentrated by evaporation. This gave 1.30 g of the crude product. 0.65 g of the crude product and 0.40 g (2.3 mmol) of 4-methanesulphonylphenylamine in 16.0 ml of acetonitrile were admixed with 0.80 ml of a 4N solution of hydrogen chloride in dioxane and stirred for 24 hours at 60° C. The mixture was admixed with a small amount of sodium hydrogen carbonate solution and concentrated in a rotary evaporator. The resulting residue was purified by means of HPLC. This gave 0.05 g (0.12 mmol) of the product.

Workup

  1. customwas admixed at 0° C.
  2. extractionExtraction
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. concentrationconcentrated in a rotary evaporator
  7. customThe resulting residue was purified by means of HPLC

Sources & evidence

ORD record
ord-3ae92e0f7a3c4ba0beed4a4c360fc33b
Source dataset
uspto-grants-2014_08
Patent number
US08802686B2

Reaction notes

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