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

HRID 1752623Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].[N:12]1([C:18]2[C:23](=[O:24])[NH:22][CH:21]=[C:20]3[CH2:25][N:26]([CH2:29][CH2:30][C:31]4[CH:40]=[CH:39][C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[N:32]=4)[C:27](=[O:28])[C:19]=23)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>C(#N)C>[CH3:5][O:4][CH2:3][CH2:2][N:22]1[C:23](=[O:24])[C:18]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[C:19]2[C:27](=[O:28])[N:26]([CH2:29][CH2:30][C:31]3[CH:40]=[CH:39][C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[N:32]=3)[CH2:25][C:20]2=[CH:21]1

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 1-bromo-2-methoxyethane (32.0 mg, 0.231 mmol), potassium carbonate (159 mg, 1.153 mmol) and 7-morpholin-4-yl-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione (90 mg, 0.231 mmol, see Example 15) were suspended in acetonitrile (50 ml) in a round-bottomed flask. The suspension was stirred at about 120° C. for about 12 h. The obtained crude material was purified by preparative HPLC to give the title compound (5 mg, 0.011 mmol, 4.84% yield).

Workup

customThe obtained crude material
customwas purified by preparative HPLC

Sources & evidence

ORD record: ord-002a728f381348e391cf12e5bfdc4d88
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163019B2

Reaction notes

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