2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one → 2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one

HRID 1509103Notes

Reaction equation

HRID 1509103 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[N:51]=[C:50]4[CH2:52][CH2:53][CH2:54][CH2:55][C:56](=[O:57])[C:49]4=[CH:48][C:47]=3[C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH: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[N:51]=[C:50]4[CH2:52][CH2:53][CH2:54][CH2:55][C:56](=[O:57])[C:49]4=[CH:48][C:47]=3[C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=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 123410895tert-butyl(1-(4-(5-oxo-3-phenyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-2-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 532619202-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-oneYield 122%

Procedure

Following the procedure for 2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one, tert-butyl(1-(4-(5-oxo-3-phenyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-2-yl)phenyl)cyclobutyl)carbamate (14 mg, 0.03 mmol) was reacted to afford the title compound as a white solid (14 mg, 100%). LCMS (Method A): RT=4.26 min, M-NH2=366. 1H NMR (500 MHz, MeOD): 8.06 (1H, s), 7.50 (2H, d), 7.42 (2H, d), 7.29-7.28 (3H, m), 7.20-7.18 (2H, m), 3.30 (2H, t), 2.89 (2H, t), 2.78-2.72 (2H, m), 2.59-2.54 (2H, m), 2.25-2.19 (1H, m), 2.06-2.01 (2H, m), 1.98-1.92 (3H, m).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-4c778992be774055814bdef84601a26c
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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