2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one → HCID 53261987, compound

HRID 1509117Notes

Reaction equation

HRID 1509117 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][N:63]=[CH:64][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>>[C:56]1([C:55]2[C:46]([C:43]3[CH:42]=[CH:41][C:40]([C:36]4([NH2:35])[CH2:39][CH2:38][CH2:37]4)=[CH:45][CH:44]=3)=[N:47][C:48]3[CH2:49][CH2:50][N:51]4[CH:64]=[N:63][N:62]=[C:52]4[C:53]=3[CH:54]=2)[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1

Participants

3

Reactant 2

HCID 532617342-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-oneHCID 123141060HCID 123141060, compound

Product 1

HCID 53261987HCID 53261987, compoundYield 127.1%

Procedure

Following the procedure for 2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one, tert-butyl(1-(4-(9-phenyl-5,6-dihydro-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)phenyl)cyclobutyl)carbamate (9 mg, 0.02 mmol) was reacted to afford the title compound (10 mg, quantitative). LCMS (Method A): RT=3.53 min, M-NH2=377. 1H NMR (500 MHz, MeOD) 8.70 (1H, s), 8.41 (1H, s), 7.52 (2H, d), 7.43 (2H, d), 7.33-7.31 (3H, m), 7.29-7.27 (2H, m), 4.57 (2H, t), 3.51 (2H, t), 2.79-2.73 (2H, m), 2.60-2.54 (2H, m), 2.27-2.20 (1H, m), 1.99-1.92 (1H, m).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-6389fbe544cc4404984ead87284e3dae
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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