2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one → HCID 53261860, compound

HRID 1509098Notes

Reaction equation

HRID 1509098 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](=[O:62])[CH2:51][C:50]([CH3:64])([CH3:63])[CH2:49][C:48]=4[N:47]=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:55]([C:56]4[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=4)=[CH:54][C:53]4[C:52](=[O:62])[CH2:51][C:50]([CH3:64])([CH3:63])[CH2:49][C:48]=4[N:47]=3)=[CH:44][CH:45]=2)[CH2:37][CH2:38][CH2:39]1

Participants

3

Reactant 2

HCID 532617342-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-oneHCID 123241448HCID 123241448, compound

Product 1

HCID 53261860HCID 53261860, compoundYield 113.5%

Procedure

Following the procedure for 2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one, tert-butyl(1-(4-(7,7-dimethyl-5-oxo-3-phenyl-5,6,7,8-tetrahydroquinolin-2-yl)phenyl)cyclobutyl)carbamate (30 mg, 0.06 mmol) was reacted to afford the title compound as a white solid (27 mg, 87%). LCMS (Method A): RT=4.48 min, M-NH2=380. 1H NMR (500 MHz, MeOD): 8.26 (1H, s), 7.50 (2H, d), 7.43 (2H, d), 7.31-7.29 (3H, m), 7.21-7.19 (2H, m), 3.15 (2H, s), 2.78-2.72 (2H, m), 2.66 (2H, s), 2.60-2.54 (2H, m), 2.27-2.18 (1H, m), 2.00-1.91 (1H, m), 1.17 (6H, s).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-e0b324b4e80c4ba4b94abae23c34c013
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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