Potassium Carbonate → HCID 25204402, compound

HRID 2079539Notes

Reaction equation

[CH3:1][N:2]1[CH2:13][CH2:12][C:5]2([NH:9][C:8](=[O:10])[NH:7][C:6]2=[O:11])[CH2:4][CH2:3]1.CS(O[CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[C:32]3[N:34]([CH3:37])[CH2:35][N:36]=[C:31]3N(C#N)C=2)=[CH:24][C:23]=1[C:40]([F:43])([F:42])[F:41])(=O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:37][N:34]1[C:32]2[CH:33]=[C:28]([C:25]3[CH:26]=[CH:27][C:22]([O:21][CH2:20][CH2:19][N:7]4[C:6](=[O:11])[C:5]5([CH2:12][CH2:13][N:2]([CH3:1])[CH2:3][CH2:4]5)[NH:9][C:8]4=[O:10])=[C:23]([C:40]([F:41])([F:42])[F:43])[CH:24]=3)[N:7]=[C:6]([C:5]#[N:9])[C:31]=2[N:36]=[CH:35]1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 8-methyl-1,3,8-triaza-spiro[4.5]decane-2,4-dione (40 mg) in DMF (0.6 mL) was added to a solution of 2-(4-(4-cyano-1-methyl-1H-imidazo[4,5-e]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)ethyl methanesulfonate (50 mg) in DMF (0.4 mL), K2CO3 (41 mg) and tetrabutyl ammonium iodide (TBAI, 26 mg). The mixture was stirred at 90° C. for 14 hours. The crude mixture was directly purified by preparative HPLC (HPLC:column XBridge MS C18 30×100 mm, 5 μm, Eluent:A:NH4HCO3, 10 mmol, pH=9.5/B:Acetonitrile, Focused gradient/8 minutes/50 mL/min) to afford 1-methyl-6-{4-[2-(8-methyl-2,4-dioxo-1,3,8-triaza-spiro[4.5]dec-3-yl)-ethoxy]-3-(trifluoromethyl)-phenyl}-1H-imidazo[4,5-c]pyridine-4-carbonitrile (20 mg).

Workup

customThe crude mixture was directly purified by preparative HPLC (HPLC
customgradient/8 minutes/50 mL/min

Sources & evidence

ORD record: ord-b1d7b1c11458494fbab359cf04da09d8
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932251B2

Reaction notes

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