Diisopropylethylamine → 1'-(5-Ethylpyrimidin-2-yl)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)-1,4'-bipiperidin-2-one

HRID 407937Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

3-(2-Fluoro-4-(methylsulfonyl)phenylamino)-1,4′-bipiperidin-2-one (0.300 g, 0.812 mmol), 2-chloro-5-ethylpyrimidine (0.116 g, 0.812 mmol) and DIEA (0.210 g, 1.62 mmol) were dissolved in DMF (5 mL) and heated at 100° C. overnight. The reaction was concentrated and purified over silica gel (50-100% EtOAc in hexanes) to provide 1′-(5-ethylpyrimidin-2-yl)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)-1,4′-bipiperidin-2-one (0.198 g, 0.416 mmol, 51.3% yield) as white solid. Mass spectrum (apci) m/z=476.2 (M+H).

Workup

concentrationThe reaction was concentrated
custompurified over silica gel (50-100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-466b6a8e2db34dc0bdca2e0937520ee5
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754226B2

Reaction notes

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