1-((1H-imidazol-2-yl)methyl)-6-(4-(1-aminocyclobutyl)phenyl)-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one → 1-(4-(1-(methylsulfonyl)-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutanamine

HRID 1509195Notes

Reaction equation

HRID 1509195 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:66]4[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=4)=[CH:54][C:55]4[N:60]([S:61]([CH3:64])(=[O:63])=[O:62])[CH2:59][CH2:58][O:57][C:56]=4[N:65]=3)=[CH:48][CH:47]=2)[CH2:45][CH2:44][CH2:43]1)(C)(C)C>>[CH3:64][S:61]([N:60]1[CH2:59][CH2:58][O:57][C:56]2[N:65]=[C:52]([C:49]3[CH:48]=[CH:47][C:46]([C:42]4([NH2:41])[CH2:45][CH2:44][CH2:43]4)=[CH:51][CH:50]=3)[C:53]([C:66]3[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=3)=[CH:54][C:55]1=2)(=[O:63])=[O:62]

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 123625959HCID 123625959, compound

Product 1

HCID 672576891-(4-(1-(methylsulfonyl)-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutanamineYield 126.3%

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-(methylsulfonyl)-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (45 mg, 0.08 mmol) was reacted to afford the title compound (44 mg, 95%). LCMS (Method A): RT=2.34 min, M+1=437. 1H NMR (500 MHz, MeOD): 8.15 (1H, s), 7.43-7.38 (4H,m), 7.30-7.28 (3H, m), 7.21-7.19 (2H, m), 4.57 (2H, t), 4.01 (2H, t), 3.19 (3H, s), 2.79-2.73 (2H, m), 2.60-2.54 (2H, m), 2.24-2.21 (1H, m), 1.99-1.94 (1H, m).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-124345dacc244e88a88ef6c2b7ec34a3
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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