HCID 53262182, compound → HCID 53262460, compound

HRID 1509240Notes

Reaction equation

HRID 1509240 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][O:64][CH3:65])[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][O:64][CH3:65])[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 123759853HCID 123759853, compound

Product 1

HCID 53262460HCID 53262460, compoundYield 64.6%

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-(methoxymethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (35 mg, 0.063 mmol) was reacted to afford the title compound (18.5 mg). 1H NMR (500 MHz, CH3OD) 7.63 (s, 1H), 7.45 (d, 2H), 7.39 (d,2H), 7.32 (m, 3H), 7.26 (m, 2H), 5.28 (t, 1H), 5.16 (dd, 2H), 4.01 (dd, 2H), 2.74-2.79 (m, 2H), 2.55-2.61 (m, 2H), 2.22-2.26 (m, 1H), 1.96-1.99 (m, 1H). LCMS (Method D): RT=0.78 min, M+H+=456.2.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-bc5675fc2c034fef985c0b118ab5c8be
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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