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

HRID 1509105Notes

Reaction equation

HRID 1509105 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])[NH:51][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:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)=[CH:54][C:53]4[C:52](=[O:62])[NH:51][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 124023320Tert-butyl(1-(4-(5-oxo-3-phenyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 532619222-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydro-1,6-naphthyridin-5(6H)-oneYield 90.2%

Procedure

Following the procedure for 2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one, tert-butyl(1-(4-(5-oxo-3-phenyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)phenyl)cyclobutyl)carbamate (10 mg, 0.021 mmol) was reacted to afford the title compound (7 mg, 69%). LCMS (Method A): RT=3.62 min, M+H+=370. 1H NMR (500 MHz, MeOD) 8.30 (1H, s), 7.51 (2H, d), 7.45 (2H, d), 7.31 (3H, m), 7.22 (2H, m), 3.70 (2H, t), 3.27(2H, t), 2.85-2.70 (2H, m), 2.65-2.50 (2H, m), 2.30-2.20 (1H, m), 2.05-1.90 (1H,m).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-eabb23ba684f468c902c3e95fc531caf
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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