Water → 4-(4-tert-Butylbenzyl)-1-(1H-pyrazolo[3,4-b]pyridin-4-yl)piperidin-4-amine

HRID 2401573Notes

Reaction equation

HRID 2401573 reaction equation
C(OC([C:6]1[C:7]([N:15]2[CH2:20][CH2:19][C:18]([NH2:32])([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)=[C:8]2[CH:14]=[N:13][NH:12][C:9]2=[N:10][CH:11]=1)=O)C.O>[OH-].[K+]>[C:28]([C:25]1[CH:26]=[CH:27][C:22]([CH2:21][C:18]2([NH2:32])[CH2:19][CH2:20][N:15]([C:7]3[CH:6]=[CH:11][N:10]=[C:9]4[NH:12][N:13]=[CH:14][C:8]=34)[CH2:16][CH2:17]2)=[CH:23][CH:24]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

4

Reactant 2

HCID 962WaterHCID 578991784-[4-Amino-4-(4-tert-butyl-benzyl)-piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 451422594-(4-tert-Butylbenzyl)-1-(1H-pyrazolo[3,4-b]pyridin-4-yl)piperidin-4-amineYield 47%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

4-[4-Amino-4-(4-tert-butyl-benzyl)-piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (23 mg, 0.053 mmol) was suspended in 2M potassium hydroxide (1 mL) and irradiated in a microwave reactor (250W) for 2 hours at 120° C. After cooling, water (2 mL) was added and the aqueous layer was extracted with ethyl acetate (2×4 mL). The organic layers were dried (Na2SO4) and concentrated to give a yellow solid (9 mg, 47%).

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×4 mL)
  3. dry with materialThe organic layers were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9c08d121b30a46e19d48c59e318c6008
Source dataset
uspto-grants-2014_08
Patent number
US08796293B2

Reaction notes

Loading…