Butylethylamine → Butyl-[3,6dimethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazolo[3,4-b]pyridin-4-yl]ethylamine

HRID 1067267Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[N:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[N:10]=[C:11]([CH3:12])[C:3]=12.[CH2:22]([NH:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25]>CS(C)=O>[CH2:22]([NH:26][CH2:27][CH2:28][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[N:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[N:10]=[C:11]([CH3:12])[C:3]=12)[CH2:23][CH2:24][CH3:25]

Participants

Conditions

Temperature: 177.5 °C

Procedure

A mixture of 4-chloro-3,6-dimethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazolo[3,4-b]pyridine (98 mg, 0.33 mmol), N-butylethylamine (1 ml) in DMSO (2 ml) was heated in an oil bath at 175-180° C. for 20 hours. The reaction mixture was quenched with saturated ammonium chloride and extracted with EtOAc. The organic layer was washed with brine, dried, and concentrated to give a brown oil. The oil residue was purified through silica gel column chromatography using EtOAc/Hexane in a ratio of 1/9 as eluent to give a colorless oil. 1H NMR (CDCl3) 6.92 (s, 2H), 6.29 (s, 1H), 3.42 (q, 2H), 3.27 (t, 2H), 2.65 (s, 3H), 2.44 (s, 3H), 2.30 (s, 3H), 1.91 (s, 6H), 1.57 (m, 2H), 1.33 (m, 2H), 1.13 (t, 3H), 0.90 (t, 3H) ppm. IR (neat) 2960, 2920, 1570 cm−1. High MS, calc. 364.2627, found 364.26306.

Workup

customThe reaction mixture was quenched with saturated ammonium chloride
extractionextracted with EtOAc
washThe organic layer was washed with brine
customdried
concentrationconcentrated
customto give a brown oil
customThe oil residue was purified through silica gel column chromatography
customto give a colorless oil

Sources & evidence

ORD record: ord-aabf28c621164bda83c82eb82cb08a7f
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248753B1

Reaction notes

Loading…