2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one → HCID 67256718, compound

HRID 1509134Notes

Reaction equation

HRID 1509134 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:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)=[CH:48][C:49]4[NH:54][CH2:53][CH2:52][O:51][C:50]=4[N:55]=3)=[CH:42][CH:41]=2)[CH2:39][CH2:38][CH2:37]1)(C)(C)C>>[C:56]1([C:47]2[C:46]([C:43]3[CH:42]=[CH:41][C:40]([C:36]4([NH2:35])[CH2:39][CH2:38][CH2:37]4)=[CH:45][CH:44]=3)=[N:55][C:50]3[O:51][CH2:52][CH2:53][NH:54][C:49]=3[CH:48]=2)[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1

Participants

3

Reactant 2

HCID 532617342-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-oneHCID 123843496HCID 123843496, compound

Product 1

HCID 67256718HCID 67256718, compoundYield 139.9%

Procedure

Following the procedure for 2-(4-(1-aminocyclobutyl)phenyl)-3-phenyl-7,8-dihydroquinolin-5(6H)-one, tert-butyl(1-(4-(7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (15 mg, 0.03 mmol) was reacted to afford the title compound (15 mg, quantitative). LCMS (Method A): RT=3.80 min, M-NH2=341. 1H NMR (500 MHz, MeOD): 7.31 (4H, s), 7.22-7.21 (3H, m), 7.12-7.11 (2H, m), 7.01 (1H, s), 4.45 (2H, t), 3.45 (2H, t), 2.75-2.70 (m, 2H), 2.56-2.50 (m, 2H), 2.24-2.15 (m, 1H), 1.97-1.88 (m, 1H).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-248b5983b8d74860bfdf26f11ee7b275
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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