Methanol → HCID 178428495, compound

HRID 1952359Notes

Reaction equation

HRID 1952359 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:12](=[O:35])[N:13]([CH2:18][CH2:19][C:20]3[C:28]4[C:23](=[N:24][CH:25]=[CH:26][CH:27]=4)[N:22](C4CCCCO4)[N:21]=3)[CH:14]=[CH:15][C:16]=2[CH3:17])[CH:9]=1)[C:5]#[N:6].CO>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:12](=[O:35])[N:13]([CH2:18][CH2:19][C:20]3[C:28]4[C:23](=[N:24][CH:25]=[CH:26][CH:27]=4)[NH:22][N:21]=3)[CH:14]=[CH:15][C:16]=2[CH3:17])[CH:9]=1)[C:5]#[N:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 685097253-chloro-5-[(4-methyl-2-oxo-1-{2-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]ethyl}-1,2-dihydropyridin-3-yl)oxy]benzonitrile

Product 1

HCID 178428495HCID 178428495, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3-chloro-5-[(4-methyl-2-oxo-1-{2-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]ethyl}-1,2-dihydropyridin-3-yl)oxy]benzonitrile (11.7 mg, 0.023 mmol) was dissolved in TFA (2 mL) and allowed to stand at room temperature for 1 hour. After this time, MeOH (1 mL) was added and the solvent evaporated in vacuo. The residue was purified on Gilson LC using a Luna reverse phase column (10μ, C18, 250×21.2 mm) and eluting with a gradient of 5-95% ACN/water (0.5% TFA). The desired fractions were combined and the solvent evaporated in vacuo to give the title compound. LRMS (M+1): 405.9.

Workup

  1. customthe solvent evaporated in vacuo
  2. customThe residue was purified on Gilson LC
  3. washeluting with a gradient of 5-95% ACN/water (0.5% TFA)
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-9b9c6a90f6bf42e099c8c34cd6b1031f
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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