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 53262056, compound

HRID 1509149Notes

Reaction equation

HRID 1509149 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:70]4[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=4)=[CH:54][C:55]4[N:60]([CH2:61][C:62]5[CH:67]=[CH:66][N:65]=[CH:64][CH:63]=5)[C:59](=[O:68])[CH2:58][O:57][C:56]=4[N:69]=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:70]4[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=4)=[CH:54][C:55]4[N:60]([CH2:61][C:62]5[CH:67]=[CH:66][N:65]=[CH:64][CH:63]=5)[C:59](=[O:68])[CH2:58][O:57][C:56]=4[N:69]=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 123782459HCID 123782459, compound

Product 1

HCID 53262056HCID 53262056, compoundYield 140.5%

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-7-phenyl-1-(pyridin-4-ylmethyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (21 mg, 0.04 mmol) was reacted to afford the title compound (26 mg, quantitative). LCMS (Method A): RT=3.25 min, M+1=464. 1H NMR (500 MHz, MeOD): 8.57 (2H, s), 7.67 (2H, s), 7.28-7.24 (4H, m), 7.23 (1H, s), 7.14-7.10 (3H, m), 6.96-6.94 (2H, m), 5.37 (2H, s), 5.03 (2H, s), 2.66-2.60 (2H, m), 2.49-2.43 (2H, m), 2.14-2.10 (1H, m), 1.89-1.82 (1H, m).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-fae10dc035ed41d99dc125e4f205348d
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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