HCID 53262182, compound → HCID 53262412, compound

HRID 1509213Notes

Reaction equation

HRID 1509213 reaction equation
NC1(C2C=CC(C3C(C4C=CC=CC=4)=CC4N(CCC#N)C(=O)COC=4N=3)=CC=2)CCC1.C(OC(=O)[NH:39][C:40]1([C:44]2[CH:49]=[CH:48][C:47]([C:50]3[C:51]([C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=4)=[CH:52][C:53]4[N:58]([CH2:59][C:60]#[N:61])[C:57](=[O:62])[CH:56]([CH2:63][CH2:64][OH:65])[O:55][C:54]=4[N:66]=3)=[CH:46][CH:45]=2)[CH2:43][CH2:42][CH2:41]1)(C)(C)C>>[NH2:39][C:40]1([C:44]2[CH:49]=[CH:48][C:47]([C:50]3[C:51]([C:67]4[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=4)=[CH:52][C:53]4[N:58]([CH2:59][C:60]#[N:61])[C:57](=[O:62])[CH:56]([CH2:63][CH2:64][OH:65])[O:55][C:54]=4[N:66]=3)=[CH:46][CH:45]=2)[CH2:41][CH2:42][CH2:43]1

Participants

3

Reactant 2

HCID 53262182HCID 53262182, compoundHCID 123866562HCID 123866562, compound

Product 1

HCID 53262412HCID 53262412, compoundYield 61.1%

Procedure

Following the procedure for 3-(6-(4-(1-aminocyclobutyl)phenyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)propanenitrile, tert-butyl(1-(4-(1-(cyanomethyl)-3-(2-hydroxyethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (15 mg, 0.027 mmol) was reacted to afford the title compound (7.5 mg). 1H NMR (500 MHz, CH3OD) 7.67 (s, 1H), 7.41 (d, 2H), 7.38 (d, 2H), 7.30 (m, 3H), 7.24 (m, 2H), 5.18 (dd, 1H), 5.11 (s, 2H), 3.81-3.89 (m, 2H), 2.71-2.77 (m, 2H), 2.52-2.58 (m, 2H), 2.27-2.30 (m, 1H), 2.16-2.23 (m, 2H), 1.93-2.10 (m, 1H). LCMS (Method A): RT=3.78 min, M+H+=456.2.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-cbfdee84181f40ecbfb0e531c5480ad4
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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