Hydrochloric Acid → HCID 117824086, compound

HRID 59068Notes

Reaction equation

HRID 59068 reaction equation
Cl.C([O:4][C:5]([C:7]1[CH:12]=[C:11]([CH:13]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[CH3:14])[N:10]=[C:9]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]3)=[C:24]([O:34][CH3:35])[CH:23]=2)[N:8]=1)=[CH2:6])C.C(=O)(O)[O-].[Na+]>O1CCOCC1.O.[Cl-].[Na+].O>[CH3:35][O:34][C:24]1[CH:23]=[C:22]([NH:21][C:9]2[N:8]=[C:7]([C:5](=[O:4])[CH3:6])[CH:12]=[C:11]([CH:13]([O:15][CH2:16][C:17]([F:18])([F:19])[F:20])[CH3:14])[N:10]=2)[CH:27]=[CH:26][C:25]=1[N:28]1[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 117824220HCID 117824220, compound

Product 1

HCID 117824086HCID 117824086, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
40 °C

Procedure

Concentrated hydrochloric acid (0.202 mL, 2.39 mmol) was added to a solution of 4-(1-ethoxy-vinyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-(1-(2,2,2-trifluoroethoxy)ethyl)-pyrimidin-2-amine (0.38 g, 0.80 mmol) in dioxane (30 mL) and water (3 mL). The solution was heated at 40° C. for 0.5 h, cooled and neutralised with sodium bicarbonate (1 g). Brine was added (5 mL) and the water phase was extracted with ethyl acetate (2×10 mL). The organic phase was dried over sodium sulfate and concentrated. The residue was purified on silica gel column using a gradient 0-4% methanol in dichloromethane as eluent to give the title compound, 330 mg (92%).

Workup

  1. extractionthe water phase was extracted with ethyl acetate (2×10 mL)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified on silica gel column

Sources & evidence

ORD record
ord-af610b9228b74e4385f79fbcf2cfc184
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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