Potassium Carbonate → 2-{4-Amino-2-[(3-chloro-4-methoxy-5-methylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-yl}-N-methylacetamide

HRID 81697Notes

Reaction equation

FC(F)(F)C(O)=O.[NH2:8][C:9]1[C:10]2[C:11]3[C:12](=[N:24][NH:25][N:26]=2)[CH:13]=[C:14]([CH2:19][C:20]([NH:22][CH3:23])=[O:21])[C:15]=3[CH2:16][S:17][N:18]=1.Cl.[Cl:28][C:29]1[C:30]([CH2:38]Cl)=[N:31][CH:32]=[C:33]([CH3:37])[C:34]=1[O:35][CH3:36].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:8][C:9]1[C:10]2[C:11]3[C:12](=[N:24][N:25]([CH2:38][C:30]4[C:29]([Cl:28])=[C:34]([O:35][CH3:36])[C:33]([CH3:37])=[CH:32][N:31]=4)[N:26]=2)[CH:13]=[C:14]([CH2:19][C:20]([NH:22][CH3:23])=[O:21])[C:15]=3[CH2:16][S:17][N:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Dimethylformamide (1 ml) was added to 2-(4-amino-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-yl)-N-methylacetamide trifluoroacetate (28 mg), 3-chloro-2-(chloromethyl)-4-methoxy-5-methylpyridine hydrochloride (36 mg), and potassium carbonate (69 mg). The resulting mixture was stirred at 60° C. for 2.5 hours. Thereafter, the insoluble matter was removed by filtration, and the solvent was then distilled away in a nitrogen stream. The resulting residue was dissolved in dimethyl sulfoxide (1 ml), and it was then purified by preparatory reverse-phase HPLC. The solvent was distilled away under reduced pressure, so as to obtain the title compound (27.0 mg) as a solid (amorphous substance).

Workup

customThereafter, the insoluble matter was removed by filtration
distillationthe solvent was then distilled away in a nitrogen stream
dissolutionThe resulting residue was dissolved in dimethyl sulfoxide (1 ml)
customit was then purified by preparatory reverse-phase HPLC
distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record: ord-f3eeb77163c44ed98820b86697c318e4
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846703B2

Reaction notes

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