Hydrochloric Acid → HCID 86725591, compound

HRID 878626Notes

Reaction equation

HRID 878626 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[CH:12]=[N:13][N:14]([C:25]2[CH:30]=[C:29]([C:31]#[N:32])[CH:28]=[CH:27][N:26]=2)[C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)(C(C)(C)C)(C)C.Cl.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>C1COCC1.O>[F:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][O:16][C:15]2[N:14]([C:25]3[CH:30]=[C:29]([C:31]#[N:32])[CH:28]=[CH:27][N:26]=3)[N:13]=[CH:12][C:11]=2[CH2:10][CH2:9][OH:8])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86725590HCID 86725590, compound

Product 1

HCID 86725591HCID 86725591, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-[4-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-5-[(4-fluorophenyl)methoxy]pyrazol-1-yl]pyridine-4-carbonitrile (60 mg, 0.13 mmol, PREPARATION 8) in THF (5 mL) was added 3N HCl (1 mL) at 0° C. The reaction mixture was stirred for 2 h at r.t. Cooled to 0° C., added ethyl acetate, water and acidified with NaHCO3 to pH=8, and the mixture was then extracted with ethyl acetate and concentrated to afford the title compound (40 mg, 91%). [M+H] Calc'd for C18H15FN4O2, 339; Found, 339.

Workup

  1. temperatureCooled to 0° C.
  2. extractionthe mixture was then extracted with ethyl acetate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f89f436cd09649bea3544c55b5454bd5
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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