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 53262568, compound

HRID 1509281Notes

Reaction equation

HRID 1509281 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:61]([CH2:62][CH2:63][F:64])[C:60](=[O:65])[CH2:59][CH2:58][NH: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:47]=[CH:48][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:61]([CH2:62][CH2:63][F:64])[C:60](=[O:65])[CH2:59][CH2:58][NH:57][C:56]=4[N:66]=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 123146761HCID 123146761, compound

Product 1

HCID 53262568HCID 53262568, compoundYield 92.9%

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-fluoroethyl)-2-oxo-8-phenyl-2,3,4,5-tetrahydro-1H-pyrido[2,3-b][1,4]diazepin-7-yl)phenyl)cyclobutyl)carbamate (15 mg, 0.03 mmol) was reacted to afford the title compound (12 mg, 64%). LCMS (Method D): RT=0.808 min, M+1=431. 1H NMR (500 MHz, MeOD): 7.76 (1H, s), 7.48 (2H, d), 7.41 (2H, d), 7.29-7.25 (3H, m), 7.20-7.18 (2H, m), 4.67 (2H, dt), 4.16 (2H, dt), 3.88-3.86 (2H, m), 2.79-2.73 (4H, m, 2.61-2.55 (2H, m), 2.25-2.18 (1H, m), 1.99-1.91 (1H, m).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-6e1ec0861d5f4ed3b769c4aacc9ca0e0
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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