6-benzyl-2-(4-(2,4-difluorophenoxy)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine → 2-(4-(2,4-difluorophenoxy)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine

HRID 713247Notes

Reaction equation

HRID 713247 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[N:11][C:12]([NH:33][CH:34]([CH3:36])[CH3:35])=[C:13]([N:18]3[CH2:23][CH2:22][CH:21]([O:24][C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=4[F:32])[CH2:20][CH2:19]3)[N:14]=2)[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[F:32][C:26]1[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:25]=1[O:24][CH:21]1[CH2:20][CH2:19][N:18]([C:13]2[N:14]=[C:15]3[CH2:16][CH2:17][NH:8][CH2:9][C:10]3=[N:11][C:12]=2[NH:33][CH:34]([CH3:36])[CH3:35])[CH2:23][CH2:22]1

Participants

4

Reactant 1

HCID 1181593036-benzyl-2-(4-(2,4-difluorophenoxy)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine

Product 1

HCID 1181591462-(4-(2,4-difluorophenoxy)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amineYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6-benzyl-2-(4-(2,4-difluorophenoxyl)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine (6.43 g, 13.03 mmol) and 10% Pd/C (640 mg) in MeOH (86 mL) under H2 in a balloon was stirred at room temperature overnight. Removal of the solvent gave the title compound (4.4 g, 84%) as a yellow oil. 1H NMR (400 MHz, methanol-d4) δ ppm 1.24 (d, J=6.4 Hz, 6H), 1.89-1.99 (m, 2H), 2.09-2.17 (m, 2H), 2.74 (t, J=5.9 Hz, 2H), 2.95 (ddd, J=12.3, 8.7, 3.4 Hz, 2H), 3.11 (t, J=6.1 Hz, 2H), 3.82 (s, 2H), 4.14 (septet, J=6.4 Hz, 1H), 4.46 (tt, J=7.7, 3.5 Hz, 1H), 6.85-6.92 (m, 1H), 6.99 (ddd, J=11.4, 8.4, 3.2 Hz, 1H), 7.18 (td, J=9.3, 5.4 Hz, 1H); ESI-MS m/z [M+H]+ 404.0.

Workup

  1. customRemoval of the solvent

Sources & evidence

ORD record
ord-aa3678f130d84a8f817029b5d60df1f9
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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