2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one → HCID 86683559, compound

HRID 1509127Notes

Reaction equation

HRID 1509127 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:60]4[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=4)=[CH:48][C:49]4[N:54]([CH2:55][C:56]#[N:57])[C:53](=[O:58])[CH2:52][O:51][C:50]=4[N:59]=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:47]([C:60]4[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=4)=[CH:48][C:49]4[N:54]([CH2:55][C:56]#[N:57])[C:53](=[O:58])[CH2:52][O:51][C:50]=4[N:59]=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 123152220HCID 123152220, compound

Product 1

HCID 86683559HCID 86683559, compoundYield 73.1%

Procedure

Following the procedure for 2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one, tert-butyl(1-(4-(1-(cyanomethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (6 mg, 0.02 mmol) was reacted to afford the title compound (6 mg, quantitative). LCMS (Method A): RT=3.95 min, M+2H+=412. 1H NMR (500 MHz, MeOD): 7.69 (1H,S), 7.43 (2H, d), 7.38 (2H, d), 7.31-7.30 (3H, m), 7.25-7.24 (m, 2H), 5.13 (2H, s), 5.03 (2H, s), 2.77-2.72 (m, 2H), 2.59-2.53 (m, 2H), 2.26-2.17 (m, 1H), 1.99-1.92 (m, 1H).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-c379a7e2983f4939aca8dd4823e585e2
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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