1-[2-Chloro-1-hydroxy-2-(1-quinolin-6-ylcyclopropyl)ethyl]pyrrolidine-2,5-dione → HCID 59420967, compound

HRID 500270Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH3:18])(=[O:16])=[O:15])=[C:10]([F:19])[CH:9]=2)=[CH:4][N:3]=1.Cl[CH:21]([C:31]1([C:34]2[CH:35]=[C:36]3[C:41](=[CH:42][CH:43]=2)[N:40]=[CH:39][CH:38]=[CH:37]3)[CH2:33][CH2:32]1)[CH:22](N1C(=O)CCC1=O)O>C(O)C>[F:19][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[N:7][C:2]3[N:3]([C:21]([C:31]4([C:34]5[CH:35]=[C:36]6[C:41](=[CH:42][CH:43]=5)[N:40]=[CH:39][CH:38]=[CH:37]6)[CH2:33][CH2:32]4)=[CH:22][N:1]=3)[CH:4]=2)[CH:13]=[CH:12][C:11]=1[S:14]([NH:17][CH3:18])(=[O:16])=[O:15]

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of 4-(2-aminopyrimidin-5-yl)-2-fluoro-N-methylbenzenesulfonamide (20 mg, 0.07 mmol) and 1-[2-chloro-1-hydroxy-2-(1-quinolin-6-ylcyclopropyl)ethyl]pyrrolidine-2,5-dione (24 mg, 0.07 mmol) in ethanol (0.4 mL) was stirred overnight at 105° C. The reaction mixture was purified by RP-HPLC (pH 10) to afford the desired product. LCMS: (M+H)=474.0.

Workup

customThe reaction mixture was purified by RP-HPLC (pH 10)

Sources & evidence

ORD record: ord-be151a66a2d248cc852b99abd1d7bda4
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Reaction notes

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