1-((1H-imidazol-2-yl)methyl)-6-(4-(1-aminocyclobutyl)phenyl)-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one → 7-(4-(1-aminocyclobutyl)phenyl)-2-methyl-8-phenyl-2,4-dihydro-1H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one

HRID 1509246Notes

Reaction equation

HRID 1509246 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:67]4[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=4)=[CH:54][C:55]4[N:60]5[C:61](=[O:65])[N:62]([CH3:64])[N:63]=[C:59]5[CH2:58][O:57][C:56]=4[N:66]=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:51]=[CH:50][C:49]([C:52]3[C:53]([C:67]4[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=4)=[CH:54][C:55]4[N:60]5[C:61](=[O:65])[N:62]([CH3:64])[N:63]=[C:59]5[CH2:58][O:57][C:56]=4[N:66]=3)=[CH:48][CH:47]=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 123631697HCID 123631697, compound

Product 1

HCID 532625107-(4-(1-aminocyclobutyl)phenyl)-2-methyl-8-phenyl-2,4-dihydro-1H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-oneYield 84.6%

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-methyl-1-oxo-8-phenyl-2,4-dihydro-1H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamate (26 mg, 0.05 mmol) was reacted to afford the title compound (18 mg, 56%). LCMS (method D): RT=0.764 min, M-NH2=409. 1H NMR (500 MHz, MeOD): 8.56 (1H, s), 7.45 (2H, d), 7.41 (2H, d), 7.33-7.31 (3H, m), 7.24-7.23 (2H, m), 5.43 (2H, s), 3.53 (3H, s), 2.78-2.72 (2H, m), 2.59-2.53 (2H, m), 2.25-2.18 (1H, m), 1.99-1.91 (1H, m).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-84782a106f56493193750ac1eebe4786
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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