Isopropyl iodide → 5-Isopropyl-7-morpholin-4-yl-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione

HRID 1752622Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].I[CH:8]([CH3:10])[CH3:9].[N:11]1([C:17]2[C:22](=[O:23])[NH:21][CH:20]=[C:19]3[CH2:24][N:25]([CH2:28][CH2:29][C:30]4[CH:39]=[CH:38][C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[N:31]=4)[C:26](=[O:27])[C:18]=23)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>C(#N)C>[CH:8]([N:21]1[C:22](=[O:23])[C:17]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)=[C:18]2[C:26](=[O:27])[N:25]([CH2:28][CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=3)[CH2:24][C:19]2=[CH:20]1)([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 105 °C

Procedure

A solution of potassium carbonate (2.5 g, 18.09 mmol), 2-iodopropane (1.0 ml, 10.00 mmol) and 7-morpholin-4-yl-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione (0.5 g, 1.281 mmol, see Example 15) were dissolved in acetonitrile (30 ml). The suspension was stirred at about 105° C. for about 24 h. After cooling to r.t., LC-MS analysis indicated complete conversion. The crude product was purified by preparative HPLC to afford the title compound (70 mg, 0.162 mmol, 12.64% yield).

Workup

temperatureAfter cooling to r.t.
customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-a9a1640b11c443ea873aa8a0e134761e
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163019B2

Reaction notes

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