Water → 4-(4-Chlorobenzyl)-1-(1H-pyrazolo[3,4-b]pyridin-4-yl)-piperidin-4-ylamine

HRID 2406010Notes

Reaction equation

HRID 2406010 reaction equation
C(OC([C:6]1[C:7]([N:15]2[CH2:20][CH2:19][C:18]([NH2:29])([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[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+]>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][C:18]2([NH2:29])[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

Participants

4

Reactant 2

HCID 962WaterHCID 578991924-[4-amino-4-(4-chlorobenzyl)-piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 451422584-(4-Chlorobenzyl)-1-(1H-pyrazolo[3,4-b]pyridin-4-yl)-piperidin-4-ylamineYield 58.5%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

4-[4-Amino-4-(4-chlorobenzyl)-piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (55 mg, 0.13 mmol) was suspended in 2M potassium hydroxide (1.5 mL) and irradiated in a microwave reactor (250 W) for 2 hours at 120° C. After cooling, water (2 mL) was added and the solids formed were collected by filtration. The filtrate was extracted with ethyl acetate (2×4 mL) and dried (Na2SO4). The extracts were evaporated and the resulting yellow solids were combined with the previous material and dissolved in acetone (10 mL) and n-hexanes (2 mL). The solvents were concentrated until precipitation occurred. The solids were collected by filtration and washed with n-hexanes to give 4-(4-chlorobenzyl)-1-(1H-pyrazolo[3,4-b]pyridin-4-yl)-piperidin-4-ylamine as a light yellow powder (26 mg, 57%). LC-MS (LCT2) m/z 342 [M+H+], Rt 2.07 min.

Workup

  1. customirradiated in a microwave reactor (250 W) for 2 hours at 120° C
  2. temperatureAfter cooling
  3. customthe solids formed
  4. filtrationwere collected by filtration
  5. extractionThe filtrate was extracted with ethyl acetate (2×4 mL)
  6. dry with materialdried (Na2SO4)
  7. customThe extracts were evaporated
  8. dissolutiondissolved in acetone (10 mL)
  9. concentrationThe solvents were concentrated until precipitation
  10. filtrationThe solids were collected by filtration
  11. washwashed with n-hexanes

Sources & evidence

ORD record
ord-a0471e493f9a41b7b4e5da5803f8d3ea
Source dataset
uspto-grants-2014_08
Patent number
US08809336B2

Reaction notes

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