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 67254897, compound

HRID 1509159Notes

Reaction equation

HRID 1509159 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]([CH2:61][CH2:62][O:63][CH3:64])[C:59](=[O:65])[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]([CH2:61][CH2:62][O:63][CH3:64])[C:59](=[O:65])[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 123692355HCID 123692355, compound

Product 1

HCID 67254897HCID 67254897, compoundYield 81.5%

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-(1-(2-methoxyethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (10 mg, 0.02 mmol) was reacted to afford the title compound (7 mg, 68%). LCMS (Method D): RT=4.11 min, M-16=423. 1H NMR (500 MHz, MeOD): 7.77 (1H,S), 7.43-7.38 (4H,m), 7.33-7.28 (3H, m), 7.23-7.21 (2H, m), 4.96 (2H, s), 4.24-4.22 (2H, t), 3.72-3.70 (2H, t), 3.36 (3H, s), 2.77-2.72 (2H, m), 2.59-2.53 (2H, m), 2.25-2.21 (1H, m), 1.98-1.94 (1H, m).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-c89a6c0c0569437fbaa807b1d520e3b4
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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