Diisopropylethylamine → HCID 54670246, compound

HRID 407917Notes

Reaction equation

Cl.[F:2][C:3]1[CH:22]=[C:21]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:20]=[CH:19][C:4]=1[O:5][C@H:6]1[C@@H:10]([OH:11])[CH2:9][N:8]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:7]1=[O:18].[Cl:27][C:28]1[CH:33]=[N:32][C:31](Cl)=[CH:30][N:29]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:27][C:28]1[N:29]=[CH:30][C:31]([N:15]2[CH2:14][CH2:13][CH:12]([N:8]3[CH2:9][C@H:10]([OH:11])[C@H:6]([O:5][C:4]4[CH:19]=[CH:20][C:21]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:22][C:3]=4[F:2])[C:7]3=[O:18])[CH2:17][CH2:16]2)=[N:32][CH:33]=1

Participants

Conditions

Temperature: 100 °C

Procedure

(3S,4S)-3-(2-fluoro-4-(methylsulfonyl)phenoxy)-4-hydroxy-1-(piperidin-4-yl)pyrrolidin-2-one hydrochloride (0.03 g, 0.073 mmol) was dissolved in DMF (2 mL) and 2,5-dichloropyrazine (0.012 g, 0.081 mmol) and Hunig's base (0.040 mL, 0.22 mmol) were added. The reaction was heated at 100° C. for 4 hours. The reaction was cooled and concentrated. The residue was purified by reverse phase chromatography (5 to 95% ACN in water) to afford (3S,4S)-1-(1-(5-chloropyrazin-2-yl)piperidin-4-yl)-3-(2-fluoro-4-(methylsulfonyl)phenoxy)-4-hydroxypyrrolidin-2-one (0.0027 g, 0.0056 mmol, 7.6% yield). Mass spectrum (apci) m/z=485.2 (M+H).

Workup

temperatureThe reaction was cooled
concentrationconcentrated
customThe residue was purified by reverse phase chromatography (5 to 95% ACN in water)

Sources & evidence

ORD record: ord-bcba2b35c79447e8a4a665a2c21600d4
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754226B2

Reaction notes

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