1-((4-methoxyphenyl)methyl)-1H-pyrazol-5-amine → tert-butyl 3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate

HRID 2383423Notes

Reaction equation

HRID 2383423 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[C:10](=[CH:15][N:16]([CH3:18])C)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:19][O:20][C:21]1[CH:33]=[CH:32][C:24]([CH2:25][N:26]2C(N)=[CH:29][CH:28]=[N:27]2)=[CH:23][CH:22]=1>>[CH3:19][O:20][C:21]1[CH:33]=[CH:32][C:24]([CH2:25][N:26]2[C:18]3[N:16]=[CH:15][C:10]4[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12][C:11]=4[C:29]=3[CH:28]=[N:27]2)=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 31612621-((4-methoxyphenyl)methyl)-1H-pyrazol-5-amineHCID 53395404tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

Product 1

HCID 59490551tert-butyl 3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate

Conditions

Temperature
130 °C

Procedure

A mixture of tert-butyl-3-((dimethylamino)methylene)-4-oxopiperidine-1-carboxylate (10.2 g, 40.15 mmol) and 1-(4-methoxybenzyl)-1H-pyrazol-5-amine (8.55 g, 42.16 mmol) were heated at 130° C. for 48 hours. The reaction mixture was cooled and the crude product was purified by flash column chromatography (SiO2, gradient from 100% CH2Cl2 to 5% MeOH in CH2Cl2) to give the desired product tert-butyl 3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate as an off white solid (3.5 g, 22%). 1H NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 7.99 (s, 1H), 7.14 (d, J=8.4 Hz, 2H), 7.81 (d, J=8.4 Hz, 2H), 5.62 (s, 2H), 4.71 (s, 2H), 3.82-3.74 (m, 5H), 3.07 (t, J=6.0 Hz, 2H), 1.44 (s, 9H). LCMS [M+H]: 395.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe crude product was purified by flash column chromatography (SiO2, gradient from 100% CH2Cl2 to 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-f4e063ab501e44f4ae2217d8709ec399
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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