2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one → HCID 67256447, compound

HRID 1509119Notes

Reaction equation

HRID 1509119 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]=[C:64]([C:65]6[N:66]=[CH:67][N:68]([CH3:70])[CH:69]=6)[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>>[CH3:70][N:68]1[CH:69]=[C:65]([C:64]2[N:51]3[C:52]([C:53]4[CH:54]=[C:55]([C:56]5[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=5)[C:46]([C:43]5[CH:42]=[CH:41][C:40]([C:36]6([NH2:35])[CH2:37][CH2:38][CH2:39]6)=[CH:45][CH:44]=5)=[N:47][C:48]=4[CH2:49][CH2:50]3)=[N:62][N:63]=2)[N:66]=[CH:67]1

Participants

3

Reactant 2

HCID 532617342-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-oneHCID 123714628HCID 123714628, compound

Product 1

HCID 67256447HCID 67256447, compoundYield 105.6%

Procedure

Following the procedure for 2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one, tert-butyl(1-(4-(3-(1-methyl-1H-imidazol-4-yl)-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): 8.43 (1H, s), 7.99 (1H, br s), 7.91 (1H, br s), 7.52 (2H, d), 7.44 (2H, d), 7.33-7.27 (5H, m), 3.89 (3H, s), 3.54 (2H, t), 3.32 (2H, t), 2.79-2.73 (2H, m), 2.61-2.55 (2H, m), 2.27-2.20 (1H, m), 2.00-1.92 (1H, m).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-cc951733cff1441d9c7dec869831c771
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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