HCID 53262182, compound → HCID 68334040, compound

HRID 1509238Notes

Reaction equation

HRID 1509238 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:63]4[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=4)=[CH:52][C:53]4[N:58]([CH3:59])[C:57](=[O:60])[C@@H:56]([CH3:61])[O:55][C:54]=4[N:62]=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:63]4[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=4)=[CH:52][C:53]4[N:58]([CH3:59])[C:57](=[O:60])[C@@H:56]([CH3:61])[O:55][C:54]=4[N:62]=3)=[CH:48][CH:49]=2)[CH2:41][CH2:42][CH2:43]1

Participants

3

Reactant 2

HCID 53262182HCID 53262182, compoundHCID 131734404HCID 131734404, compound

Product 1

HCID 68334040HCID 68334040, compoundYield 50.8%

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, (R)-tert-butyl(1-(4-(1,3-dimethyl-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (16 mg, 0.032 mmol) was reacted to afford the title compound (6.5 mg). 1H NMR (500 MHz, CH3OD) 7.56 (s, 1H), 7.42 (d, 2H), 7.38 (d, 2H), 7.31 (m, 3H), 7.24 (m, 2H), 5.06 (q, 1H), 3.44 (s, 3H), 2.73-2.77 (m, 2H), 2.53-2.59 (m, 2H), 2.20-2.26 (m, 1H), 1.95-1.97 (m, 1H), 1.67 (d, 3H). LCMS (Method D): RT=0.85 min, M+H+=400.2.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-e70d984983d943a5b7dd763834ab0dc3
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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