2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one → 1-(4-(6-Ethyl-3-phenyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)phenyl)cyclobutanamine

HRID 1509115Notes

Reaction equation

HRID 1509115 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[CH2:52][N:51]([CH2:62][CH3:63])[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>>[CH2:62]([N:51]1[CH2:50][CH2:49][C:48]2[N:47]=[C:46]([C:43]3[CH:44]=[CH:45][C:40]([C:36]4([NH2:35])[CH2:37][CH2:38][CH2:39]4)=[CH:41][CH:42]=3)[C:55]([C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)=[CH:54][C:53]=2[CH2:52]1)[CH3:63]

Participants

3

Reactant 2

HCID 532617342-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-oneHCID 123698040Tert-butyl(1-(4-(6-ethyl-3-phenyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 672621871-(4-(6-Ethyl-3-phenyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)phenyl)cyclobutanamineYield 156.4%

Procedure

Following the procedure for 2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one, tert-butyl(1-(4-(6-ethyl-3-phenyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)phenyl)cyclobutyl)carbamate (14 mg, 0.03 mmol) was reacted to afford the title compound (18 mg, quantitative). LCMS (Method A): RT=0.44 min, M-NH2=367. 1H NMR (500 MHz, MeOD) 7.76 (1H, s), 7.45 (2H, d), 7.42 (2H, d), 7.30-7.29 (3H, m), 7.19-7.18 (2H, m), 3.47 (2H, q), 3.46 (2H, t), 3.39 (2H, br s), 3.32 (2H, m), 2.77-2.71 (2H, m), 2.60-2.54 (2H, m), 2.27-2.18 (1H, m), 1.99-1.90 (1H, m), 1.50 (3H, t).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-3b2d7ee17c364c56aeef14d85adc1b0c
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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