Triethylamine → methyl 2-[1-[4-(2-naphthamido)benzyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]acetate

HRID 589411Notes

Reaction equation

HRID 589411 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[C:9]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[N:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][C:31]=1[C:40](Cl)=[O:41]>ClCCl>[CH:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][C:31]=1[C:40]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[C:9]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[N:8]2)=[CH:21][CH:22]=1)=[O:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 89590257methyl 2-[1-(4-aminobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]acetate

Product 1

HCID 90449071methyl 2-[1-[4-(2-naphthamido)benzyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]acetateYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-[1-(4-aminobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]acetate (58 mg, 0.20 mmol) and triethylamine (41 mg, 0.41 mmol) were dissolved in 15 mL dichloromethane. In an ice bath, 2-naphthoyl chloride (38 mg, 0.20 mmol) was added. Upon completion of addition, it was moved to react at room temperature for 1 hour. It was rotate evaporated to dryness to remove the solvent, and chromatographed on a column (PE:EA=15:1) to obtain a white oil 60 mg, at a yield of 65%.

Workup

  1. additionUpon completion of addition, it
  2. customto react at room temperature for 1 hour
  3. customIt was rotate evaporated to dryness
  4. customto remove the solvent
  5. customchromatographed on a column (PE:EA=15:1)

Sources & evidence

ORD record
ord-3b998724106a435491e5453831d43437
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

Loading…