1-(3-Aminopropyl)-2-pyrrolidinone → HCID 58168032, compound

HRID 1029298Notes

Reaction equation

HRID 1029298 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.[NH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:25][CH2:24][CH2:23][C:22]1=[O:26]>>[O:26]=[C:22]1[CH2:23][CH2:24][CH2:25][N:21]1[CH2:20][CH2:19][CH2:18][NH:17][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 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 581682989-chloro-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168032HCID 58168032, compoundYield 7%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 456 using 6 (160 mg, 0.69 mmol) and 1-(3-aminopropyl)pyrrolidin-2-one (395 mg, 2.78 mmol) to provide 479 (15 mg, 7% yield) as a white powder. LC-MS (M+H=337, obsd.=337). 1H NMR (400 MHz, DMSO-D6) δ 11.47 (s, 1H), 8.67 (d, J=7.7, 1H), 8.43 (d, J=3.2, 1H), 7.99 (d, J=8.8, 1H), 7.19 (m, 2H), 6.90 (dd, J=1.9, 8.7, 1H), 6.64 (s, 1H), 3.27 (m, 4H), 3.24 (s, 2H), 2.23 (t, J=8.0, 2H), 1.87 (m, 2H), 1.73 (m, 2H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-df7674b844804235b342a9d88a34e9e7
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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