Sodium Hydroxide → HCID 67124417, compound

HRID 476115Notes

Reaction equation

HRID 476115 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, 9H), 2.60 (s, 3H), 7.60 (dd, J=7.96, 4.67 Hz, 1H), 8.08 (s, 1H), 8.57 (dt, J=8.34, 1.89 Hz, 1H), 8.70 (dd, J=4.80, 1.52 Hz, 1H), 9.39 (d, J=1.52 Hz, 1H), 14.03 (br. s., 1H).

Workup

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

Sources & evidence

ORD record
ord-feb82c2d8e4e453d9ef7488623e37c70
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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