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 86683602, compound

HRID 1509200Notes

Reaction equation

HRID 1509200 reaction equation
N1C=CN=C1CN1C(=O)COC2N=C(C3C=CC(C4(N)CCC4)=CC=3)C(C3C=CC=CC=3)=CC1=2.[CH3:35][N:36]1[CH2:41][C:40](=[O:42])[NH:39][C:38]2[CH:43]=[C:44]([C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)[C:45]([C:47]3[CH:52]=[CH:51][C:50]([C:53]4([NH:57]C(=O)OC(C)(C)C)[CH2:56][CH2:55][CH2:54]4)=[CH:49][CH:48]=3)=[N:46][C:37]1=2>>[NH2:57][C:53]1([C:50]2[CH:49]=[CH:48][C:47]([C:45]3[C:44]([C:65]4[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=4)=[CH:43][C:38]4[NH:39][C:40](=[O:42])[CH2:41][N:36]([CH3:35])[C:37]=4[N:46]=3)=[CH:52][CH:51]=2)[CH2:54][CH2:55][CH2:56]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 67256554HCID 67256554, compound

Product 1

HCID 86683602HCID 86683602, compoundYield 125.7%

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-(4-methyl-2-oxo-7-phenyl-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-6-yl)phenyl)cyclobutylcarbamate (29 mg, 0.060 mmol) was reacted to afford the title compound (29 mg, 97%). LCMS (Method A): RT=3.69 min, M+2H+=386. 1H NMR (500 MHz, MeOD): 7.44 (2H, d), 7.32 (2H, d), 7.20-7.28 (3H, m), 7.12 (2H, d), 7.02 (1H, s), 4.08 (2H, s), 3.11 (3H, s), 2.70-2.80 (2H, m), 2.50-2.63 (2H, m), 2.13-2.27 (1H, m), 1.88-2.02 (1H, m).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-b2429baa530945c39d1fabb43e27afef
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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