Trifluoroacetic acid → Methyl 5-[4-fluoro-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]pyrazolo[1,5-a]pyridin-5-yl]-2-methoxy-6-methyl-3-pyridinecarboxylate

HRID 2068425Notes

Reaction equation

HRID 2068425 reaction equation
C(O[C:6]([N:8](C)[C:9]([C:11]1[C:12]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)=[N:13][N:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:21]([CH3:32])=[N:22][C:23]([O:30][CH3:31])=[C:24]([CH:29]=3)[C:25]([O:27][CH3:28])=[O:26])=[C:16]([F:33])[C:15]=12)=[O:10])=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[F:33][C:16]1[C:15]2[N:14]([N:13]=[C:12]([C:34]3[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=3)[C:11]=2[C:9](=[O:10])[NH:8][CH3:6])[CH:19]=[CH:18][C:17]=1[C:20]1[C:21]([CH3:32])=[N:22][C:23]([O:30][CH3:31])=[C:24]([CH:29]=1)[C:25]([O:27][CH3:28])=[O:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59411413HCID 59411413, compound

Product 1

HCID 59411422Methyl 5-[4-fluoro-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]pyrazolo[1,5-a]pyridin-5-yl]-2-methoxy-6-methyl-3-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing methyl 5-(3-(tert-butoxycarbonyl(methyl)carbamoyl)-4-fluoro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl)-2-methoxy-6-methylnicotinate (0.07 g, 0.13 mmol) and dichloromethane (2.5 mL) was added TFA (0.39 mL, 5.0 mmol) at room temperature. The solution was maintained for 15 minutes and concentrated to dryness to afford Methyl 5-(4-fluoro-2-(4-fluorophenyl)-3-(methylcarbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-2-methoxy-6-methylnicotinate as a tan solid which was used without further purification. LCMS retention time: 1.777 min. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna, 10 micron, C18, 3.0×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% methanol/90% H2O/10 mM TFA and solvent B was 10% H2O/90% methanol/10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode. m/z 489 (MNa+).

Workup

  1. temperatureThe solution was maintained for 15 minutes
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f2b3405d38844477925740a31a68c95b
Source dataset
uspto-grants-2012_10
Patent number
US08293909B2

Reaction notes

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