2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one → 2-(2-(4-(1-aminocyclobutyl)phenyl)-5-oxo-3-phenyl-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)acetonitrile

HRID 1509109Notes

Reaction equation

HRID 1509109 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](=[O:62])[N:51]([CH2:63][C:64]#[N:65])[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:41]=[CH:42][C:43]([C:46]3[C:55]([C:56]4[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=4)=[CH:54][C:53]4[C:52](=[O:62])[N:51]([CH2:63][C:64]#[N:65])[CH2:50][CH2:49][C:48]=4[N:47]=3)=[CH:44][CH:45]=2)[CH2:39][CH2:38][CH2:37]1

Participants

3

Reactant 2

HCID 532617342-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-oneHCID 131734399Tert-butyl(1-(4-(6-(cyanomethyl)-5-oxo-3-phenyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 532619232-(2-(4-(1-aminocyclobutyl)phenyl)-5-oxo-3-phenyl-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)acetonitrileYield 122.4%

Procedure

Following the procedure for 2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one, tert-butyl(1-(4-(6-(cyanomethyl)-5-oxo-3-phenyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)phenyl)cyclobutyl)carbamate (17 mg, 0.03 mmol) was reacted to afford the title compound (15 mg, 71%). LCMS (Method A): RT=3.80 min, M-NH2=392. 1H NMR (500 MHz, MeOD): 8.33 (1H, S), 7.50 (2H, d), 7.42 (2H, d), 7.31-7.29 (3H, m), 7.22-7.20 (m, 2H), 4.66 (2H, s), 3.92 (2H, t), 3.38 (2H, t), 2.78-2.72 (m, 2H), 2.60-2.54 (m, 2H), 2.27-2.18 (m, 1H), 2.00-1.91 (m, 1H).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-1c0ed293f79e400b9cca5d7f501ff2e9
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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