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)-8-phenyl-2-(2,2,2-trifluoroethyl)-2,4-dihydro-1H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one

HRID 1509254Notes

Reaction equation

HRID 1509254 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:71]4[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=4)=[CH:54][C:55]4[N:60]5[C:61](=[O:69])[N:62]([CH2:64][C:65]([F:68])([F:67])[F:66])[N:63]=[C:59]5[CH2:58][O:57][C:56]=4[N:70]=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:71]4[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=4)=[CH:54][C:55]4[N:60]5[C:61](=[O:69])[N:62]([CH2:64][C:65]([F:66])([F:67])[F:68])[N:63]=[C:59]5[CH2:58][O:57][C:56]=4[N:70]=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 123765621HCID 123765621, compound

Product 1

HCID 532625127-(4-(1-aminocyclobutyl)phenyl)-8-phenyl-2-(2,2,2-trifluoroethyl)-2,4-dihydro-1H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-oneYield 86.1%

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-oxo-8-phenyl-2-(2,2,2-trifluoroethyl)-2,4-dihydro-1H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamate (45 mg, 0.08 mmol) was reacted to afford the title compound (34 mg, 61%). LCMS (Method D): RT=0.923 min, M-NH2=477. 1H NMR (500 MHz, MeOD): 8.43 (1H, s), 7.34-7.28 (4H, m), 7.21-7.20 (3H, m), 7.13-7.12 (2H, m), 5.34 (2H, s), 4.49 (2H, q), 2.70-2.62 (2H, m), 2.49-2.43 (2H, m), 2.15-2.08 (1H, m), 1.91-1.77 (1H, m).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-c1e1621de3d14f44be157935734938c8
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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