Sodium Hydroxide → HCID 67124417, compound

HRID 1522507Notes

Reaction equation

HRID 1522507 reaction equation
[CH3:1][C:2]([N:5]1[C:9]2[N:10]=[C:11]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:12]=[C:13]([C:14]([O:16]CC)=[O:15])[C:8]=2[C:7]([CH3:25])=[N:6]1)([CH3:4])[CH3:3].[OH-].[Na+]>C(O)C>[CH3:4][C:2]([N:5]1[C:9]2[N:10]=[C:11]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:12]=[C:13]([C:14]([OH:16])=[O:15])[C:8]=2[C:7]([CH3:25])=[N:6]1)([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68079252HCID 68079252, compound

Product 1

HCID 67124417HCID 67124417, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-(1,1-dimethylethyl)-3-methyl-6-(3-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (68 mg, 0.201 mmol) was suspended in ethanol (2 mL) followed by addition of sodium hydroxide (0.335 mL, 1.005 mmol). The mixture was stirred at room temperature for 2. 5 h. The mixture was concentrated and the residue was diluted with water (1 mL) and acidified to pH 3 using 1N HCl. The precipitate was collected by filtration and further dried under high vacuum to give the product as an HCl salt, 60 mg (86%). LCMS E-S (M+H)=311.5. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.82 (s, 9 H), 2.60 (s, 3 H), 7.60 (dd, J=7.96, 4.67 Hz, 1 H), 8.08 (s, 1 H), 8.57 (dt, J=8.34, 1.89 Hz, 1 H), 8.70 (dd, J=4.80, 1.52 Hz, 1 H), 9.39 (d, J=1.52 Hz, 1 H), 14.03 (br. s., 1 H).

Workup

  1. custom5 h
  2. concentrationThe mixture was concentrated
  3. additionthe residue was diluted with water (1 mL)
  4. filtrationThe precipitate was collected by filtration
  5. customfurther dried under high vacuum

Sources & evidence

ORD record
ord-5f056ee18b6c4647848c6af0f2cad2a1
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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