2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one → 8(4-(1-aminocyclobutyl)phenyl)-9-phenyl-5,6-dihydro-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-3(2H)-one

HRID 1509113Notes

Reaction equation

HRID 1509113 reaction equation
NC1(C2C=CC(C3C(C4C=CC=CC=4)=CC4C(=O)CCCC=4N=3)=CC=2)CCC1.C(OC(=O)[NH:35][C:36]1([C:40]2[CH:45]=[CH:44][C:43]([C:46]3[C:55]([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)=[CH:54][C:53]4[C:52]5=[N:62][NH:63][C:64](=[O:65])[N:51]5[CH2:50][CH2:49][C:48]=4[N:47]=3)=[CH:42][CH:41]=2)[CH2:39][CH2:38][CH2:37]1)(C)(C)C>>[NH2:35][C:36]1([C:40]2[CH:45]=[CH:44][C:43]([C:46]3[C:55]([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)=[CH:54][C:53]4[C:52]5=[N:62][NH:63][C:64](=[O:65])[N:51]5[CH2:50][CH2:49][C:48]=4[N:47]=3)=[CH:42][CH:41]=2)[CH2:37][CH2:38][CH2:39]1

Participants

3

Reactant 2

HCID 532617342-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-oneHCID 123922000Tert-butyl(1-(4-(3-oxo-9-phenyl-2,3,5,6-tetrahydro-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 532619258(4-(1-aminocyclobutyl)phenyl)-9-phenyl-5,6-dihydro-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-3(2H)-oneYield 77.1%

Procedure

Following the procedure for 2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one, tert-butyl(1-(4-(3-oxo-9-phenyl-2,3,5,6-tetrahydro-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)phenyl)cyclobutyl)carbamate (10 mg, 0.019 mmol) was reacted to afford the title compound (6 mg, 58%). LCMS (Method A): RT=3.51 min, M+2=411.2. 1H NMR (500 MHz, MeOD): 8.23 (1H, S), 7.52 (2H, d), 7.43 (2H, d), 7.34-7.32 (3H, m), 7.26-7.24 (2H, m), 4.09 (2H, t), 3.46 (2H, t), 2.81-2.75 (2H, m), 2.62-2.56 (2H, m), 2.28-2.22 (1H, m), 2.01-1.95 (1H, m).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-364e024d80604424809919ec87fdb677
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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