N-methyl-2-pyrrolidone → HCID 25181651, compound

HRID 1896022Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[N:3]=1.Br[C:18]1[CH:19]=[N:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1.CCN(C(C)C)C(C)C.CN1CCCC1=O>CCOC(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:12][CH2:13][N:14]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=3)[CH2:15][CH2:16]2)[N:3]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A vial was filled with a mixture of the compound of Example 3 (84.9 mg, 0.4 mmol), 3-bromo-5-(trifluoromethyl)pyridine (93 mg, 0.4 mmol), DIPEA (140 μL, 0.8 mmol), 1 mL of anhydrous N-methylpyrrolidone and sealed. The vial was heated in a microwave oven at 160° C. (200 W) for 2 h. The reaction mixture was then cooled to r.t., diluted with EtOAc, washed with water, dried over Na2SO4 and evaporated to dryness in vacuo. The crude black oily residue was purified by preparative RP LC-MS chromatography, using MS-C18 XTerra column 30×50 mm eluting with ammonium bicarbonate 20 mM pH 8 buffer-acetonitrile gradient affording 1.8 mg of the title compound.

Workup

customsealed
temperatureThe reaction mixture was then cooled to r.t.
washwashed with water
dry with materialdried over Na2SO4
customevaporated to dryness in vacuo
customThe crude black oily residue was purified by preparative RP LC-MS chromatography
washeluting with ammonium bicarbonate 20 mM pH 8 buffer-acetonitrile gradient

Sources & evidence

ORD record: ord-6188b5095eef44d397b0d1f49dbe526d
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518916B2

Reaction notes

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