1-((1H-imidazol-2-yl)methyl)-6-(4-(1-aminocyclobutyl)phenyl)-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one → HCID 53261685, compound

HRID 1509257Notes

Reaction equation

HRID 1509257 reaction equation
N1C=CN=C1CN1C(=O)COC2N=C(C3C=CC(C4(N)CCC4)=CC=3)C(C3C=CC=CC=3)=CC1=2.C(OC(=O)[NH:41][C:42]1([C:46]2[CH:51]=[CH:50][C:49]([C:52]3[C:53]([C:64]4[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=4)=[CH:54][C:55]4[NH:61][C:60](=[O:62])[CH2:59][CH2:58][NH:57][C:56]=4[N:63]=3)=[CH:48][CH:47]=2)[CH2:45][CH2:44][CH2:43]1)(C)(C)C>>[NH2:41][C:42]1([C:46]2[CH:47]=[CH:48][C:49]([C:52]3[C:53]([C:64]4[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=4)=[CH:54][C:55]4[NH:61][C:60](=[O:62])[CH2:59][CH2:58][NH:57][C:56]=4[N:63]=3)=[CH:50][CH:51]=2)[CH2:45][CH2:44][CH2:43]1

Participants

3

Reactant 2

HCID 532620541-((1H-imidazol-2-yl)methyl)-6-(4-(1-aminocyclobutyl)phenyl)-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-oneHCID 123453589HCID 123453589, compound

Product 1

HCID 53261685HCID 53261685, compoundYield 108.4%

Procedure

Following the procedure for 1-((1H-imidazol-2-yl)methyl)-6-(4-(1-aminocyclobutyl)phenyl)-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one, tert-butyl(1-(4-(2-oxo-8-phenyl-2,3,4,5-tetrahydro-1H-pyrido[2,3-b][1,4]diazepin-7-yl)phenyl)cyclobutyl)carbamate (27 mg, 0.06 mmol) was reacted to afford the title compound (25 mg, 73%). LCMS (Method D): RT=0.644 min, M+1=385. 1H NMR (500 MHz, MeOD): 7.47-7.43 (5H, m), 7.27-7.25 (3H, m), 7.16-7.14 (2H, m), 3.78-3.76 (2H, m), 2.90-2.88 (2H, m), 2.79-2.73 (2H, m), 2.62-2.56 (2H, m), 2.26-2.22 (1H, m), 1.99-1.95 (1H, m).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-290b4e0e441c45b781d326c1091ab8c6
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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