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 68299633, compound

HRID 1509261Notes

Reaction equation

HRID 1509261 reaction equation
N1C=CN=C1CN1C(=O)C[O:10][C:9]2N=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:69]4[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=4)=[CH:54][C:55]4[N:60]([CH2:61][C:62]5([CH3:66])C[O:64][CH2:63]5)[C:59](=[O:67])[CH2:58][O:57][C:56]=4[N:68]=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:69]4[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=4)=[CH:54][C:55]4[N:60]([CH2:61][C:62]([CH2:9][OH:10])([CH3:66])[CH2:63][OH:64])[C:59](=[O:67])[CH2:58][O:57][C:56]=4[N:68]=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 123395621tert-butyl(1-(4-(1-((3-methyloxetan-3-yl)methyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 68299633HCID 68299633, compoundYield 79%

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-methyloxetan-3-yl)methyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (16 mg, 0.03 mmol) was reacted to afford the title compound (16 mg, 79%). LCMS (Method D): RT=0.721 min, M+1=474. 1H NMR (500 MHz, MeOD): 8.03 (1H,S), 7.44-7.38 (4H,m), 7.30-7.24 (5H, m), 4.96 (2H, s), 4.11 (2H, s), 3.47-3.41 (4H, m), 2.77-2.72 (2H, m), 2.59-2.53 (2H, m), 2.25-2.21 (1H, m), 1.98-1.94 (1H, m), 0.92 (3H, s).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-03ec57fafacf4fb581f975c7bf669a98
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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