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

HRID 1752620Notes

Reaction equation

COC1C=CC(C[N:8]2[C:13](=[O:14])[C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[C:11]3[C:21](=[O:36])[N:22]([CH2:24][CH2:25][C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=4)[CH2:23][C:10]3=[CH:9]2)=CC=1>C(O)(C(F)(F)F)=O>[N:15]1([C:12]2[C:13](=[O:14])[NH:8][CH:9]=[C:10]3[CH2:23][N:22]([CH2:24][CH2:25][C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=4)[C:21](=[O:36])[C:11]=23)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

Conditions

Temperature: 100 °C

Procedure

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 (30 mg, 0.059 mmol, see Example 14) was dissolved in TFA (30 ml), stirred and heated to about 100° C. for about 12 h. LC-MS analysis indicated complete conversion. The crude material was purified via preparative thin-layer chromatography (MeOH/DCM=10:90) to give the title compound (17 mg, 0.043 mmol, 73.4% yield).

Workup

customThe crude material was purified via preparative thin-layer chromatography (MeOH/DCM=10:90)

Sources & evidence

ORD record: ord-b61f23016aca47348935b3f6331afade
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163019B2

Reaction notes

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