Water → 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-5-methylbenzoic acid

HRID 564502

Reaction equation

HRID 564502 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:34][CH3:35])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:24]=[C:25]([CH:30]=[C:31]([CH3:33])[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+]>O1CCCC1>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:34][CH3:35])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:24]=[C:25]([CH:30]=[C:31]([CH3:33])[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

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57813541Methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-5-methylbenzoate

Product 1

HCID 578133503-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-5-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-5-methylbenzoate (3.49 g, 7.28 mmol) was dissolved in tetrahydrofuran (THF) (90 ml) and water (30.0 ml) was added. Lithium hydroxide (0.458 g, 10.92 mmol) was added and the mixture stirred under argon at room temperature overnight. The THF was rotavaped off, and the aqueous residue was adjusted to ˜pH of 6 with 1N HCL. A white solid formed and was filtered and washed 2× with water (10 mL). This solid was dried at 50° C. in a vacuum oven for 6 h to give the title compound as a white solid. LC-MS m/z 466.0 (M+H)+, 0.73 min (ret time); mp 236-239° C.; analytical HPLC shows 97.3% purity, (ret time 10.841 min).

Workup

  1. customA white solid formed
  2. filtrationwas filtered
  3. washwashed 2× with water (10 mL)
  4. customThis solid was dried at 50° C. in a vacuum oven for 6 h

Sources & evidence

ORD record
ord-bb1ae5ced5654c99b7ccb7e2e875c47a
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Linked notes

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