Potassium Phosphate, Tribasic → HCID 118092601, compound

HRID 2207396Notes

Reaction equation

F[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]([NH:15][C:16]3[N:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][N:17]=3)[CH:11]=[C:12]([CH3:14])[CH:13]=2)[CH:5]=[CH:4][N:3]=1.[N:26]1([C:32](=[O:34])[CH3:33])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CS(C)=O>[CH3:14][C:12]1[CH:13]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([N:29]3[CH2:30][CH2:31][N:26]([C:32](=[O:34])[CH3:33])[CH2:27][CH2:28]3)[CH:7]=2)[CH:9]=[C:10]([NH:15][C:16]2[N:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][N:17]=2)[CH:11]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of N-[3-(2-fluoropyridin-4-yl)-5-methylphenyl]-4-(trifluoromethyl)pyrimidin-2-amine (50.0 mg, 0.144 mmol), 1-(piperazin-1-yl)ethanone (36.8 mg, 0.287 mmol), and tribasic potassium phosphate (60.9 mg, 0.287 mmol) in DMSO (250 μL) was heated at 130° C. for 48 hours. The reaction mixture was diluted with DMSO (600 μL) and filtered through a plug of CELITE. The residue was purified by mass triggered reverse phase HPLC (21-55% acetonitrile in water+0.1% formic acid) to afford 1-{4-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]piperazin-1-yl}ethanone as a tan solid. MS APCI calc'd for C23H24F3N6O [M+H]+ 457. found 457. 1H NMR (600 MHz, DMSO-d6) δ10.20 (s, 1H), 8.80 (d, J=4.8 Hz, 1H), 8.15 (d, J=5.2 Hz, 1H), 7.99 (s, 1H), 7.53 (s, 1H), 7.24 (d, J=4.9 Hz, 1H), 7.22 (s, 1H), 6.98 (s, 1H), 6.88 (d, J=5.3 Hz, 1H), 3.62-3.56 (m, 2H), 3.52 (d, J=7.5 Hz, 6H), 2.34 (s, 3H), 2.02 (s, 3H).

Workup

filtrationfiltered through a plug of CELITE
customThe residue was purified by mass triggered reverse phase HPLC (21-55% acetonitrile in water+0.1% formic acid)

Sources & evidence

ORD record: ord-457bbc6d932444a4b85c1dfe6575cf89
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376418B2

Reaction notes

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