HCID 53262182, compound → HCID 68299609, compound

HRID 1509165Notes

Reaction equation

HRID 1509165 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:65]4[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=4)=[CH:52][C:53]4[N:58]([CH:59]([C:61]#[N:62])[CH3:60])[C:57](=[O:63])[CH2:56][O:55][C:54]=4[N:64]=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:45]=[CH:46][C:47]([C:50]3[C:51]([C:65]4[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=4)=[CH:52][C:53]4[N:58]([CH:59]([CH3:60])[C:61]#[N:62])[C:57](=[O:63])[CH2:56][O:55][C:54]=4[N:64]=3)=[CH:48][CH:49]=2)[CH2:41][CH2:42][CH2:43]1

Participants

3

Reactant 2

HCID 53262182HCID 53262182, compoundHCID 123922698HCID 123922698, compound

Product 1

HCID 68299609HCID 68299609, compoundYield 99.7%

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-(1-cyanoethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (7 mg, 0.013 mmol) was reacted to afford the title compound (5.5 mg). 1H NMR (500 MHz, CH3OD) 7.77 (1H, s), 7.44 (2H, d), 7.40 (2H, d), 7.30-7.34 (3H, m), 7.25-7.28 (2H, m), 6.03 (1H, q), 4.99 (2H, s), 2.7-2.85 (2H, m), 2.55-2.65 (2H, m), 2.2-2.3 (1H, m), 1.9-2.1 (1H, m), 1.81 (3H, d), LCMS (Method A): RT=4.11 min, M+H+=426.1.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-a3cc7646487a4fcd8c51e7f7579e870e
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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