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Triethylamine → 4-[4-amino-4-(4-chlorobenzyl)-piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

HRID 2406009
Notes
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Reaction equation

HRID 2406009 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[C:8]2[CH:14]=C[NH:12][C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2].Cl.[Cl:17][C:18]1[CH:31]=[CH:30][C:21]([CH2:22][C:23]2([NH2:29])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:20][CH:19]=1.C([N:34](CC)CC)C>C(O)CCC.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([N:26]2[CH2:25][CH2:24][C:23]([NH2:29])([CH2:22][C:21]3[CH:20]=[CH:19][C:18]([Cl:17])=[CH:31][CH:30]=3)[CH2:28][CH2:27]2)=[C:8]2[CH:14]=[N:34][NH:12][C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 53438275Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylateHCID 668730314-(4-Chlorobenzyl)-piperidin-4-ylamine hydrochloride

Product 1

HCID 578991924-[4-amino-4-(4-chlorobenzyl)-piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl esterYield 87%

Reagents, catalysts & solvents 2

HCID 263
1-Butanol
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid ethyl ester (Example 68A) (50 mg, 0.22 mmol), 4-(4-chlorobenzyl)-piperidin-4-ylamine hydrochloride (65 mg, 0.22 mmol) and triethylamine (150μ) in n-butanol (1.5 mL) was irradiated in a microwave reactor (200 W) for 1 hr at 100° C. After cooling, the solvent was evaporated. The solids obtained were dissolved in ethyl acetate, the organic layer was washed with aqueous sodium hydrogen carbonate, brine and then dried (Na2SO4). Evaporation of the organic solution gave 4-[4-amino-4-(4-chlorobenzyl)-piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester as an off-white solid (80 mg, 87%). LC-MS (LCT2) m/z 415 [M+H+], Rt 3.99 min.

Workup

  1. customwas irradiated in a microwave reactor (200 W) for 1 hr at 100° C
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. customThe solids obtained
  5. washthe organic layer was washed with aqueous sodium hydrogen carbonate, brine
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the organic solution

Sources & evidence

ORD record
ord-90e353220fa04123852e642074158a64
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08809336B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes