Hydrochloric Acid → HCID 59741003, compound

HRID 2192178Notes

Reaction equation

HRID 2192178 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[C:17]([F:18])=[CH:16][C:15]([NH:19]C(=O)C(F)(F)F)=[CH:14][C:13]=2[F:26])[N:4](COCC[Si](C)(C)C)[CH:3]=1.Cl.[OH-].[Li+]>O1CCOCC1.O>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[C:17]([F:18])=[CH:16][C:15]([NH2:19])=[CH:14][C:13]=2[F:26])[NH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59741005HCID 59741005, compound

Product 1

HCID 59741003HCID 59741003, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 201 mg of N-{4-[(3-bromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3,5-difluorophenyl}-2,2,2-trifluoroacetamide (280 μmol) in 4.00 ml of a mixture of hydrogen chloride in dioxane (4N) is stirred at RT overnight, and the precipitated crystals are filtered off and washed with diethyl ether. The solid residue (131 mg) is dissolved in 20 ml of THF. 2.7 ml of a 5% strength solution of lithium hydroxide in water (5.62 mmol) are then added, and the mixture is stirred at RT for 60 h. The reaction mixture is diluted with water and extracted twice with ethyl acetate. After drying over magnesium sulfate, the combined organic phases are concentrated and the residue is purified by preparative HPLC.

Workup

  1. filtrationthe precipitated crystals are filtered off
  2. washwashed with diethyl ether
  3. dissolutionThe solid residue (131 mg) is dissolved in 20 ml of THF
  4. extractionextracted twice with ethyl acetate
  5. dry with materialAfter drying over magnesium sulfate
  6. concentrationthe combined organic phases are concentrated
  7. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-851e73ddb5034bd7b9d26cc4e57bea79
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

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