2-(Quinolin-2-yl)ethan-1-amine → 7-Chloro-5-methyl-2-(2-(quinolin-2-YL)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-C]pyridine-1,6(5H)-dione

HRID 1752600Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][NH2:13].[CH3:14][N:15]1[CH:20]=[C:19]([CH2:21]Cl)[C:18]([C:23](OC)=[O:24])=[C:17]([Cl:27])[C:16]1=[O:28]>CCO>[Cl:27][C:17]1[C:16](=[O:28])[N:15]([CH3:14])[CH:20]=[C:19]2[CH2:21][N:13]([CH2:12][CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)[C:23](=[O:24])[C:18]=12

Participants

Conditions

Temperature: 80 °C

Procedure

TEA (4.18 ml, 30.0 mmol) and 2-quinolin-2-yl-ethanamine (1.89 g, 11 mmol, see Example a1)) were each rapidly added in sequence to a suspension of 1-methyl-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-5-chloromethyl-pyridine (2.5 g, 10.00 mmol, see compound (6) of Example b1.5)) in EtOH (10 ml). The reaction was heated in a microwave at about 80° C. for about 20 min. The reaction was cooled to r.t. and the mixture was filtered and washed with a little EtOH to afford the title compound (1.35 g, 38.2% yield). MS (ESI+): m/e 418 (M+H)+, Rt:1.67 min; 1H-NMR (400 MHz, CDCl3): δ=3.28 (t, J=7.2 Hz, 2H); 3.53 (s, 3H); 3.97 (t, J=7.2 Hz, 2H); 4.31 (s, 2H); 7.49 (d, J=8.4 Hz, 1H); 7.56 (t, J=7.3 Hz, 1H); 7.73 (t, J=7.6 Hz, 1H); 7.92-7.95 (m, 2H); 7.98 (s, 1H); 8.30 (d, J=8.4 Hz, 1H).

Workup

temperatureThe reaction was cooled to r.t.
filtrationthe mixture was filtered
washwashed with a little EtOH

Sources & evidence

ORD record: ord-1d32c04e9fa04ab89e6ce8e1df605945
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163019B2

Reaction notes

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