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 53261679, compound

HRID 1509232Notes

Reaction equation

HRID 1509232 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:65]4[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=4)=[CH:54][C:55]4[N:56]([CH3:64])[C:57](=[O:63])[N:58]([CH3:62])[CH2:59][C:60]=4[N:61]=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:65]4[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=4)=[CH:54][C:55]4[N:56]([CH3:64])[C:57](=[O:63])[N:58]([CH3:62])[CH2:59][C:60]=4[N:61]=3)=[CH:50][CH:51]=2)[CH2:43][CH2:44][CH2:45]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 123485213HCID 123485213, compound

Product 1

HCID 53261679HCID 53261679, compoundYield 117.1%

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-(1,3-dimethyl-2-oxo-7-phenyl-1,2,3,4-tetrahydropyrido[3,2-d]pyrimidin-6-yl)phenyl)cyclobutyl)carbamate (30 mg, 0.06 mmol) was reacted to afford the title compound (28 mg, 91%). LCMS (Method D): R1=0.798 min, M-NH2=382. 1H NMR (500 MHz, MeOD): 7.45-7.39 (4H, m), 7.34 (1H, s), 7.32-7.30 (3H, m), 7.26-7.24 (2H, m), 4.67 (2H, s), 3.36 (3H, s), 3.11 (3H, s), 2.81-2.75 (2H, m), 2.63-2.57 (2H, m), 2.26-2.24 (1H, m), 1.99-1.97 (1H, m).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-45612a3fd15e4e71acea0fee196809a7
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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