Diisopropylethylamine → (S)-3-(1H-indazol-5-yloxy)-1-(1-(5-chloropyrazin-2-yl)piperidin-4-yl)pyrrolidin-2-one

HRID 407968Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A flask was charged with (S)-3-(1H-indazol-5-yloxy)-1-(piperidin-4-yl)pyrrolidin-2-one (0.120 g, 0.400 mmol), 2,5-dichloropyrazine (0.0655 g, 0.439 mmol), DIEA (d 0.742) (0.0696 mL, 0.400 mmol), and DMF (3 mL). The reaction was stirred at 100° C. overnight. The organic solvents were removed under reduced pressure. The residue was purified using preparative TLC with 10% methanol in ethyl acetate to provide (S)-3-(1H-indazol-5-yloxy)-1-(1-(5-chloropyrazin-2-yl)piperidin-4-yl)pyrrolidin-2-one (0.0047 g, 0.0114 mmol, 2.85% yield). Mass spectrum (apci) m/z=413.2 (M+H).

Workup

customThe organic solvents were removed under reduced pressure
customThe residue was purified

Sources & evidence

ORD record: ord-b566ad88c8634a7991a8c7df59a1a921
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754226B2

Reaction notes

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