1-(6-(4-(1-aminocyclobutyl)phenyl)-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)ethanone → HCID 53262055, compound

HRID 1509147Notes

Reaction equation

HRID 1509147 reaction equation
NC1(C2C=CC(C3C(C4C=CC=CC=4)=CC4N(C(=O)C)CC[O:17]C=4N=3)=CC=2)CCC1.N1C=CN=C1CCN1C(=O)COC2N=C(C3C=CC(C4(N)CCC4)=CC=3)C(C3C=CC=CC=3)=CC1=2.C(OC(=O)[NH:72][C:73]1([C:77]2[CH:82]=[CH:81][C:80]([C:83]3[C:84]([C:96]4[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=4)=[CH:85][C:86]4[N:91]([CH2:92][C:93]#[N:94])[CH2:90][CH2:89][O:88][C:87]=4[N:95]=3)=[CH:79][CH:78]=2)[CH2:76][CH2:75][CH2:74]1)(C)(C)C>>[NH2:72][C:73]1([C:77]2[CH:78]=[CH:79][C:80]([C:83]3[C:84]([C:96]4[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=4)=[CH:85][C:86]4[N:91]([CH2:92][C:93]([NH2:94])=[O:17])[CH2:90][CH2:89][O:88][C:87]=4[N:95]=3)=[CH:81][CH:82]=2)[CH2:76][CH2:75][CH2:74]1

Participants

4

Reactant 3

HCID 532620521-(6-(4-(1-aminocyclobutyl)phenyl)-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)ethanoneHCID 86683574HCID 86683574, compoundHCID 123741605HCID 123741605, compound

Product 1

HCID 53262055HCID 53262055, compound

Procedure

Following the procedure for 1-(6-(4-(1-aminocyclobutyl)phenyl)-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)ethanone, 1-((1H-imidazol-2-yl)ethyl)-6-(4-(1-aminocyclobutyl)phenyl)-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one, tert-butyl(1-(4-(1-(cyanomethyl)-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (5 mg, 0.01 mmol) was reacted to afford the two title compounds (1 mg, 25% and 2 mg, 41%). LCMS: RT=3.99 min, M-16=380. 1H NMR (500 MHz, MeOD): 7.20-7.13 (8H, m), 7.09-7.07 (2H, m), 4.46 (2H, t), 3.54 (2H, s), 3.22 (2H, t), 2.46-2.40 (2H, m), 2.17-2.11 (2H, m), 1.97-1.94 (1H, m), 1.66-1.62 (1H, m). LCMS (Method A): RT=3.99 min, M-16=398. 1H NMR (500 MHz, D2O): 8.39 (2H, s), 7.27-7.22 (7H, m), 7.11-7.09 (2H, m), 6.89 (1H, s), 4.78 (2H, s), 4.48 (2H, t), 4.00 (2H, s), 3.50 (2H, t), 2.65-2.60 (2H, m), 2.53-2.47 (2H, m), 2.09-2.05 (1H, m), 1.86-1.79 (1H, m).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-c41932be8a9840e9a8dea1956215f320
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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