4-Pyridinemethanamine → 2-(4-Tert-butyl-phenyl)-1-hydroxy-4-[(pyridin-4-ylmethyl)-amino]-1,2-dihydro-pyrrolo[3,4-c)pyridin-3-one

HRID 2251856Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:19]([OH:20])[C:18]3[CH:17]=[CH:16][N:15]=[C:14](F)[C:13]=3[C:12]2=[O:22])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:23][CH2:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1>CCN(C(C)C)C(C)C.C(O)CCC>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:19]([OH:20])[C:18]3[CH:17]=[CH:16][N:15]=[C:14]([NH:23][CH2:24][C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[C:13]=3[C:12]2=[O:22])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 2-(4-tert-butyl-phenyl)-4-fluoro-1-hydroxy-1,2-dihydro-pyrrolo[3,4-c]pyridin-3-one (0.11 g, 0.38 mmol, Step B) and 4-(aminomethyl)pyridine (0.070 mL, 0.68 mmol) in 0.70 mL of DIEA and 1.0 ml of BuOH was subjected to microwave heating at 170° C. for 17 min. The volatiles were removed under reduced pressure, and the residue was purified by flash column chromatography (0 to 5% of MeOH in CH2Cl2) to provide the titled compound as an off-white solid. MS (ES+): 389.1 (M+H)+. Calc'd for C23H24N4O2-388.46.

Workup

customThe volatiles were removed under reduced pressure
customthe residue was purified by flash column chromatography (0 to 5% of MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-4be41bdf31d8443a85ee2a8e836b9f90
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320992B2

Reaction notes

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