2-(3,5-dimethylpiperidin-1-yl)ethanamine → HCID 58168018, compound

HRID 1029297Notes

Reaction equation

HRID 1029297 reaction equation
Cl[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.[CH3:17][CH:18]1[CH2:23][CH:22]([CH3:24])[CH2:21][N:20]([CH2:25][CH2:26][NH2:27])[CH2:19]1>>[CH3:17][CH:18]1[CH2:23][CH:22]([CH3:24])[CH2:21][N:20]([CH2:25][CH2:26][NH:27][C:2]2[CH:16]=[CH:15][C:5]3[C:6](=[O:14])[NH:7][C:8]4[C:13]([C:4]=3[CH:3]=2)=[CH:12][CH:11]=[CH:10][N:9]=4)[CH2:19]1

Participants

3

Reactant 2

HCID 64841772-(3,5-dimethylpiperidin-1-yl)ethanamineHCID 581682989-chloro-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168018HCID 58168018, compoundYield 9%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 456 using 6 (171 mg, 0.74 mmol) and 2-(3,5-dimethylpiperidin-1-yl)ethanamine (464 mg, 2.97 mmol) to provide 478 (23 mg, 9% yield) as a white powder. LC-MS (M+H=351, obsd.=351). 1H NMR (400 MHz, DMSO-D6) δ 11.58 (s, 1H), 9.48 (s, 1H), 8.73 (d, J=6.7, 1H), 8.46 (dd, J=1.6, 4.7, 1H), 8.06 (d, J=8.7, 1H), 7.42 (d, J=2.1, 1H), 7.29 (dd, J=4.7, 7.9, 1H), 6.96 (dd, J=2.1, 8.8, 1H), 3.70 (s, 2H), 3.52 (d, J=11.1, 2H), 3.30 (d, J=5.3, 2H), 2.56 (dt, J=8.1, 16.4, 2H), 1.89 (s, 2H), 1.77 (d, J=13.0, 1H), 0.91 (t, J=8.4, 6H), 0.80 (dd, J=12.3, 24.8, 1H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-d4d9751fd49144348abfc68244d42ffa
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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