2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one → HCID 67257365, compound

HRID 1509131Notes

Reaction equation

HRID 1509131 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:47]([C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=4)=[CH:48][C:49]4[N:54]([CH2:55][C:56]([NH2:58])=[O:57])[C:53](=[O:59])[CH2:52][O:51][C:50]=4[N:60]=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:45]=[CH:44][C:43]([C:46]3[C:47]([C:61]4[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=4)=[CH:48][C:49]4[N:54]([CH2:55][C:56]([NH2:58])=[O:57])[C:53](=[O:59])[CH2:52][O:51][C:50]=4[N:60]=3)=[CH:42][CH:41]=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 123987634HCID 123987634, compound

Product 1

HCID 67257365HCID 67257365, compoundYield 116.7%

Procedure

Following the procedure for 2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one, tert-butyl(1-(4-(1-(2-amino-2-oxoethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (10 mg, 0.02 mmol) was reacted to afford the title compound (10 mg, quantitative). LCMS (Method A): RT=3.43 min, M-NH2=412. 1H NMR (500 MHz, MeOD): 7.39 (2H, d), 7.36 (2H, d), 7.34 (1H,S), 7.28-7.26 (3H, m), 7.18-7.17 (m, 2H), 5.01 (2H, s), 4.72 (2H, s), 2.76-2.70 (m, 2H), 2.57-2.51 (m, 2H), 2.25-2.16 (m, 1H), 1.98-1.89 (m, 1H).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-3666d3ad9da449878e8b7cc3d5570fa1
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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