2-(2-Aminoethyl)-1-methylpyrrolidine → HCID 58168371, compound

HRID 1029294Notes

Reaction equation

HRID 1029294 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][N:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[CH2:23][CH2:24][NH2:25]>>[CH3:17][N:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[CH2:23][CH2:24][NH:25][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

Participants

3

Reactant 2

HCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 581682989-chloro-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168371HCID 58168371, compoundYield 25.2%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 456 using 6 (100 mg, 0.43 mmol) and 2-(1-methyl-pyrrolidin-2-yl)ethanamine (0.25 mL, 1.73 mmol) to provide 475 (35 mg, 25% yield) as a white powder. LC-MS (M+H=322, obsd.=322). 1H NMR (400 MHz, DMSO-D6) δ 11.47 (s, 1H), 8.65 (d, J=8.1, 1H), 8.43 (d, J=4.7, 1H), 7.99 (d, J=8.8, 1H), 7.18 (m, 2H), 6.89 (d, J=8.8, 1H), 6.65 (s, 1H), 3.24 (s, 2H), 2.98 (m, 1H), 2.25 (d, J=1.4, 3H), 2.02 (m, 2H), 1.97 (s, 2H), 1.66 (s, 2H), 1.52 (s, 2H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-2d829042743a4a088b60d65e23d5386b
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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