Potassium Carbonate → 3-Chloro-4-{3-isopropyl-4-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzamide

HRID 1625245Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[C:14]2=[N:15][CH:16]=[CH:17][C:18](Cl)=[C:13]2[C:12]([CH:20]([CH3:22])[CH3:21])=[N:11]1)[C:5]#[N:6].C(=O)([O-])[O-:24].[K+].[K+].Cl.[CH3:30][N:31]1[CH:35]=[C:34]([C:36]2[N:37]=[CH:38][NH:39][CH:40]=2)[CH:33]=[N:32]1>CS(C)=O.C(Cl)(Cl)Cl.[Cu]=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[C:14]2=[N:15][CH:16]=[CH:17][C:18]([N:39]3[CH:40]=[C:36]([C:34]4[CH:33]=[N:32][N:31]([CH3:30])[CH:35]=4)[N:37]=[CH:38]3)=[C:13]2[C:12]([CH:20]([CH3:22])[CH3:21])=[N:11]1)[C:5]([NH2:6])=[O:24]

Participants

Conditions

Temperature: 120 °C

Procedure

Compound (99a) (0.18 g) was dissolved in DMSO (2.1 mL), and potassium carbonate (0.3 g), copper(II) oxide (nanopowder) (0.086 g), and 4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazole hydrochloride (0.13 g) were added to the resulting solution, followed by stirring at 120° C. for 48 hr. The reaction solution was diluted with chloroform, and insoluble matters were filtered by celite. The solvent was distilled away, and the residue was purified by neutral silica gel column chromatography (chloroform/methanol) to obtain compound (99) (0.045 g, 18%) as a white solid.

Workup

filtrationwere filtered by celite
distillationThe solvent was distilled away
customthe residue was purified by neutral silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record: ord-04cb45c77d654a45aa3ea1de5b434c31
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779142B2

Reaction notes

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