Dimethylamine → HCID 11648254, compound

HRID 1693507Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[C:6]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[N:5]=[C:4]2[N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:23]=[CH:24][C:3]=12.[CH3:31][NH:32][CH3:33]>>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[C:2]([N:32]([CH3:33])[CH3:31])=[C:3]3[CH:24]=[N:23][N:22]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:4]3=[N:5][C:6]=2[C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[CH:9][CH:10]=1

Participants

Reactant 2

HCID 674Dimethylamine

HCID 57898125HCID 57898125, compound

Product 1

HCID 11648254HCID 11648254, compoundYield 73%

Procedure

4-Chloro-5,6-bis-(4-chloro-phenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridine from step A (15 mg, 0.033 mmol) is treated with dimethylamine (2 M in THF, 1 mL, 2 mmol) in a sealed tube at 100° C. for 14 h. After cooling down to room temperature, the mixture is concentrated and the residue is purified by flash column chromatography (silica gel, 0%˜15% EtOAc/hex) to provide the titled compound [5,6-Bis-(4-chloro-phenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl]-dimethyl-amine (11 mg, 73%). 1H NMR (CDCl3) δ(ppm) 8.35 (s, 1H), 8.32 (d, 2H), 7.47(t, 2H), 7.27(t, 1H), 7.23(d, 2H), 7.16(d, 2H), 7.11(d, 2H), 7.03(d, 2H), 2.91(s, 6H); HPLC-MS calculated for C26H20Cl2N4 (M+H+): 459.1. Found: 459.1.

Workup

concentrationthe mixture is concentrated
customthe residue is purified by flash column chromatography (silica gel, 0%˜15% EtOAc/hex)

Sources & evidence

ORD record: ord-f2f186d34ec5426b9d998c6b9e0b39a8
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158634B2

Reaction notes

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