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 53261682, compound

HRID 1509265Notes

Reaction equation

HRID 1509265 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:69]4[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=4)=[CH:54][C:55]4[N:56]([CH2:66][CH2:67][F:68])[C:57](=[O:65])[N:58]([CH2:62][CH2:63][F:64])[CH2:59][C:60]=4[N:61]=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:69]4[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=4)=[CH:54][C:55]4[N:56]([CH2:66][CH2:67][F:68])[C:57](=[O:65])[N:58]([CH2:62][CH2:63][F:64])[CH2:59][C:60]=4[N:61]=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 131734406HCID 131734406, compound

Product 1

HCID 53261682HCID 53261682, compoundYield 36%

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-bis(2-fluoroethyl)-2-oxo-7-phenyl-1,2,3,4-tetrahydropyrido[3,2-d]pyrimidin-6-yl)phenyl)cyclobutyl)carbamate (15 mg, 0.03 mmol) was reacted to afford the title compound (5 mg, 27%). LCMS (Method D): RT=0.872 min, M-NH2=446. 1H NMR (500 MHz, MeOD): 7.52 (1H, s), 7.45-7.39 (4H, m), 7.32-7.30 (3H, m), 7.24-7.22 (2H, m), 4.81-4.77 (4H, m), 4.68 (2H, dt), 4.28 (2H, dt), 3.83 (2H, dt), 2.81-2.75 (2H, m), 2.63-2.57 (2H, m), 2.26-2.24 (1H, m), 1.99-1.97 (1H, m).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-eb5a08057b4c4d739d37f919daf5015d
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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