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

HRID 1470293Notes

Reaction equation

HRID 1470293 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.[C:17]([C:21]1[CH:34]=[CH:33][C:24]([CH2:25][C:26]2([NH2:32])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18].C([N:37](CC)CC)C>C(O)CCC>[CH2:1]([O:3][C:4]([C:6]1[C:7]([N:29]2[CH2:30][CH2:31][C:26]([NH2:32])([CH2:25][C:24]3[CH:33]=[CH:34][C:21]([C:17]([CH3:20])([CH3:18])[CH3:19])=[CH:22][CH:23]=3)[CH2:27][CH2:28]2)=[C:8]2[CH:14]=[N:37][NH:12][C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53438275Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylateHCID 668725374-(4-Tert-butyl-benzyl)-piperidin-4-ylamine hydrochloride

Product 1

HCID 578991784-[4-Amino-4-(4-tert-butyl-benzyl)-piperidin-1-yl]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

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-tert-butyl-benzyl)-piperidin-4-ylamine hydrochloride (70.8 mg, 0.22 mmol) and triethylamine (150 μL) in n-butanol (1.5 mL) was irradiated in a microwave reactor (200 W) for 1 hour at 100° C. After cooling, the solvent was evaporated and the residue was purified by column chromatography (EtOAc-MeOH 4:1) to give an off-white solid (63 mg, 65%). LC-MS (LCT2) m/z 436 [M+H+], Rt 5.01 min.

Workup

  1. customwas irradiated in a microwave reactor (200 W) for 1 hour at 100° C
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. customthe residue was purified by column chromatography (EtOAc-MeOH 4:1)

Sources & evidence

ORD record
ord-5f831d1aafff4198b85325167366a9e2
Source dataset
uspto-grants-2015_04
Patent number
US09006430B2

Reaction notes

Loading…