Water → HCID 178465999, compound

HRID 1050179Notes

Reaction equation

HRID 1050179 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([NH:29][C:30]3[NH:34][N:33]=[C:32]([C:35]([CH3:41])([CH3:40])[C:36]([F:39])([F:38])[F:37])[CH:31]=3)=[O:28])=[C:22]([F:42])[CH:21]=2)[CH:7]=[N:8][C:9]=1[O:10]CC1C=CC(OC)=CC=1)[CH3:2].C(Cl)[Cl:44].O.C(#N)C>C(O)(C(F)(F)F)=O>[ClH:44].[CH2:1]([O:3][C:4]1[C:9](=[O:10])[NH:8][CH:7]=[C:6]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([NH:29][C:30]3[NH:34][N:33]=[C:32]([C:35]([CH3:41])([CH3:40])[C:36]([F:38])([F:39])[F:37])[CH:31]=3)=[O:28])=[C:22]([F:42])[CH:21]=2)[CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 6344DichloromethaneHCID 178465998HCID 178465998, compound

Product 1

HCID 178465999HCID 178465999, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)-N-(3-(1,1,1-trifluoro-2-methylpropan-2-yl)-1H-pyrazol-5-yl)acetamide (100 mg, 0.170 mmol) in TFA.DCM (solvate) (10 mL, 10%) was stirred for 0.5 h at 25° C. Then the mixture was concentrated to give a residue which purified by preparative HPLC (column: ASB C18 150*25 mm/Mobile phase A: Water(Water+0.1% HCl)/Mobile phaseB: Acetonitrile/Gradient: 33-63 (B %)/Flowrate: 25 mL/min/Run time: 15 min) to yield a white solid of 2-(4-(5-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)-N-(3-(1,1,1-trifluoro-2-methylpropan-2-yl)-1H-pyrazol-5-yl)acetamide hydrochloride (43.33 mg, 0.084 mmol, 49.2% yield): 1H NMR (400 MHz, DMSO-d6) δ 11.81 (s, 1H), 10.68 (s, 1H), 7.46-7.28 (m, 5H), 7.11 (d, J=2.0 Hz, 1H), 6.41 (s, 1H), 4.03 (q, J=6.8 Hz, 2H), 3.66 (s, 2H), 1.45 (s, 6H), 1.32 (t, J=6.9 Hz, 3H). ES-LCMS m/z 467 (M+H).

Workup

  1. concentrationThen the mixture was concentrated
  2. customto give a residue which
  3. custompurified by preparative HPLC (column

Sources & evidence

ORD record
ord-48566bfad9224d86b13b3e4727af6e03
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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