HCID 53262182, compound → HCID 53262456, compound

HRID 1509226Notes

Reaction equation

HRID 1509226 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:64]4[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=4)=[CH:52][C:53]4[N:58]([CH2:59][CH2:60][F:61])[C:57](=[O:62])[CH2:56][O:55][C:54]=4[N:63]=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:64]4[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=4)=[CH:52][C:53]4[N:58]([CH2:59][CH2:60][F:61])[C:57](=[O:62])[CH2:56][O:55][C:54]=4[N:63]=3)=[CH:48][CH:49]=2)[CH2:43][CH2:42][CH2:41]1

Participants

3

Reactant 2

HCID 53262182HCID 53262182, compoundHCID 123982281HCID 123982281, compound

Product 1

HCID 53262456HCID 53262456, compoundYield 104.3%

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-fluoroethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (60 mg, 0.116 mmol) was reacted to afford the title compound (50.5 mg). 1H NMR (500 MHz, CH3OD) 7.69 (1H, s), 7.42 (2H, d), 7.38 (2H, d), 7.30 (3H, m), 7.22 (2H, m), 4.99 (2H, s), 4.80 (1H, t), 4.70 (1H, t), 4.40 (1H, t), 4.35 (1H, t), 2.73-2.79 (2H, m), 2.54-2.60 (2H, m), 2.20-2.25 (1H, m), 1.95-1.97 (1H, m). LCMS (Method D): RT=0.83 min, M+H+=418.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-060ed10d6397471e8e5a1d386cf6c252
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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