HCID 53262182, compound → HCID 86683618, compound

HRID 1509224Notes

Reaction equation

HRID 1509224 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]([CH2:59][CH:60]([F:62])[F:61])[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: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]([CH2:59][CH:60]([F:62])[F:61])[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

Participants

3

Reactant 2

HCID 53262182HCID 53262182, compoundHCID 123893239HCID 123893239, compound

Product 1

HCID 86683618HCID 86683618, compoundYield 99.3%

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-(2,2-difluoroethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (20 mg, 0.037 mmol) was reacted to afford the title compound (16 mg). 1H NMR (500 MHz, CH3OD) 7.71 (s, 1H), 7.42 (d, 2H), 7.38 (d, 2H), 7.31 (m, 3H), 7.22 (m, 2H), 6.21 (tt, 1H), 5.01 (s, 2H), 4.50 (dt, 2H), 2.73-2.78 (m, 2H), 2.54-2.59 (m, 2H), 2.21-2.25 (m, 1H), 1.93-1.99 (m, 1H). LCMS (Method D): RT=0.84 min, M+H+=436.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-6f5022b96a7c4cf784c1088a1adc57c0
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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