HCID 53262182, compound → HCID 68299636, compound

HRID 1509211Notes

Reaction equation

HRID 1509211 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]([CH3:59])[C:57](=[O:60])[CH:56]([CH2:61][CH2:62][OH:63])[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:49]=[CH:48][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]([CH3:59])[C:57](=[O:60])[CH:56]([CH2:61][CH2:62][OH:63])[O:55][C:54]=4[N:64]=3)=[CH:46][CH:45]=2)[CH2:41][CH2:42][CH2:43]1

Participants

3

Reactant 2

HCID 53262182HCID 53262182, compoundHCID 124016986HCID 124016986, compound

Product 1

HCID 68299636HCID 68299636, compoundYield 53.4%

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-(3-(2-hydroxyethyl)-1-methyl-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (12.5 mg, 0.024 mmol) was reacted to afford the title compound (5.5 mg). 1H NMR (500 MHz, CH3OD) 7.64 (s, 1H), 7.41 (m, 4H), 7.28 (m, 3H), 7.18 (m, 2H), 5.09 (dd, 1H), 3.80-3.92 (m, 2H), 3.41 (s, 1H), 2.72 (m, 2H), 2.54 (m, 2H), 2.24 (m, 2H), 2.13 (m, 1H), 1.94 (m, 1H). LCMS (Method A): RT=3.76 min, M+H+=413.16.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-a2c6a1268935496e9d28ac9be22d3485
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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