Hydrochloric Acid → 3-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic Acid

HRID 564542Notes

Reaction equation

HRID 564542 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:33][CH3:34])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=3)[C:26]([O:28]C)=[O:27])=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].O.[OH-].[Li+].Cl>CO.O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:33][CH3:34])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=3)[C:26]([OH:28])=[O:27])=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 57813262Methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoate

Product 1

HCID 578132773-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoate (3.02 g, 0.0064 mol) in MeOH (30 mL) was stirred with lithium hydroxide monohydrate (1.36 g, 0.032 mol) in H2O (15 mL) overnight at room temperature. The solution was treated with 3N HCl to adjust the pH to about 2.0 and cooled in an ice bath. Solid was collected and dried (2.4 g). The filtrate was treated with sat. aq. NaCl and extracted with EtOAc (2×). The extract was dried (Na2SO4) and concentrated to a residue. It was triturated with ether to afford the title compound as a white solid (143 mg only slightly inferior to the main product by LC-MS). Total product 2.56 g (88.7%). LC-MS m/z 452.1 (M+H)+.

Workup

  1. temperaturecooled in an ice bath
  2. customSolid was collected
  3. customdried (2.4 g)
  4. additionThe filtrate was treated with sat. aq. NaCl
  5. extractionextracted with EtOAc (2×)
  6. dry with materialThe extract was dried (Na2SO4)
  7. concentrationconcentrated to a residue
  8. customIt was triturated with ether

Sources & evidence

ORD record
ord-a227f203a55748b8b3f8c95eaa075b64
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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