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

HRID 1752619Notes

Reaction equation

Cl[C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:5]=[C:4]2[CH2:18][N:19]([CH2:22][CH2:23][C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)[C:20](=[O:21])[C:3]=12.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:6]2[C:7](=[O:8])[C:2]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[C:3]3[C:20](=[O:21])[N:19]([CH2:22][CH2:23][C:24]4[CH:33]=[CH:32][C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]=4)[CH2:18][C:4]3=[CH:5]2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 7-chloro-5-(4-methoxy-benzyl)-2-(2-quinolin-2-yl-ethyl)-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione (65 mg, 0.141 mmol, see Example c7)), morpholine (12.31 mg, 0.141 mmol), Xantphos (82 mg, 0.141 mmol), palladium diacetate (31.7 mg, 0.141 mmol) and Cs2CO3 (138 mg, 0.424 mmol) in dioxane (5 ml) was heated in a CEM microwave at about 120° C. for about 30 min. The solvent was removed and the crude material was purified via preparative thin-layer chromatography (MeOH/DCM=5:95) to give the title compound (30 mg, 0.056 mmol, 39.5% yield).

Workup

customThe solvent was removed
customthe crude material was purified via preparative thin-layer chromatography (MeOH/DCM=5:95)

Sources & evidence

ORD record: ord-afff9f16ec1941a6acae0c6be6d4f8aa
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163019B2

Reaction notes

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