HCID 57403866, compound → HCID 57400314, compound

HRID 1968554Notes

Reaction equation

HRID 1968554 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[C:16]([NH:25][C:26]3[N:31]=[C:30]([C:32]4[N:33]([CH3:40])[CH:34]=[C:35]([C:37](=[O:39])[NH2:38])[CH:36]=4)[CH:29]=[CH:28][N:27]=3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>O1CCOCC1.Cl>[CH3:40][N:33]1[C:32]([C:30]2[CH:29]=[CH:28][N:27]=[C:26]([NH:25][C:16]3[CH:15]=[C:14]([N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:19]=[CH:18][C:17]=3[O:20][C:21]([F:24])([F:23])[F:22])[N:31]=2)=[CH:36][C:35]([C:37]([NH2:38])=[O:39])=[CH:34]1

Participants

4

Reactant 1

HCID 57403866HCID 57403866, compound

Product 1

HCID 57400314HCID 57400314, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 4-{3-[4-(4-carbamoyl-1-methyl-1H-pyrrol-2-yl)-pyrimidin-2-ylamino]-4-trifluoromethoxy-phenyl}-piperazine-1-carboxylic acid tert-butyl ester (176 mg, 0.314 mmol) in dioxane (3 mL), HCl in dioxane solution (4N, 4 mL) were added. The reaction was stirred at room temperature for 6 hours and the precipitate collected by filtration. The precipitate was dissolved in HCl water solution (0.1N, 30 mL) and washed with dichlorometane (50 mL). The aqueous layers were collected and the title compound precipitated by addition of sodium bicarbonate. The aqueous phase was eliminated by filtration, the solid washed with water (10 mL) and dried under vacuo at 30° C. to yield 96 mg (66%) of the title compound as an hazelnut powder.

Workup

  1. filtrationthe precipitate collected by filtration
  2. dissolutionThe precipitate was dissolved in HCl water solution (0.1N, 30 mL)
  3. washwashed with dichlorometane (50 mL)
  4. customThe aqueous layers were collected
  5. customthe title compound precipitated by addition of sodium bicarbonate
  6. filtrationThe aqueous phase was eliminated by filtration
  7. washthe solid washed with water (10 mL)
  8. customdried under vacuo at 30° C.

Sources & evidence

ORD record
ord-da7a6dc9f47743a599f9c49ad7346b8c
Source dataset
uspto-grants-2013_04
Patent number
US08426417B2

Reaction notes

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