2,4-Dimethoxybenzylamine → HCID 178490966, compound

HRID 1499732Notes

Reaction equation

HRID 1499732 reaction equation
Cl[C:2]1[C:7]2[C:8]([CH3:11])=[N:9][NH:10][C:6]=2[CH:5]=[N:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[CH2:22][NH2:23]>C(O)CCC>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[CH2:22][NH:23][C:2]1[CH:3]=[N:4][CH:5]=[C:6]2[NH:10][N:9]=[C:8]([CH3:11])[C:7]=12

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 178434369HCID 178434369, compound

Product 1

HCID 178490966HCID 178490966, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 4-chloro-3-methyl-1H-pyrazolo[4,3-d]pyridine (330 mg, 1.9 mmol) and 1-(2,4-dimethoxyphenyl)methanamine (0.58 mL, 3.9 mmol) in 1-butanol was heated in the microwave at 150° C. for 40 minutes. Purification via preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) gave the desired product (240 mg, 42%). LCMS for C16H19N4O2 (M+H)+: m/z=299.1; Found: 299.2.

Workup

  1. customPurification via preparative LCMS (XBridge C18 column
  2. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-7c7afdc3103d406bbbc0325668bd4a97
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

Loading…