HCID 53262182, compound → HCID 68299621, compound

HRID 1509241Notes

Reaction equation

HRID 1509241 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][O:62][CH3:63])[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][O:62][CH3:63])[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 123245956HCID 123245956, compound

Product 1

HCID 68299621HCID 68299621, compoundYield 98.8%

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, tert-butyl(1-(4-(3-(methoxymethyl)-1-methyl-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (35 mg, 0.066 mmol) was reacted to afford the title compound (28 mg). 1H NMR (500 MHz, CH3OD) 7.49 (s, 1H), 7.42 (d, 2H), 7.38 (d,2H), 7.31 (m, 3H), 7.25 (m, 2H), 5.19 (t, 1H), 4.02 (dd, 1H), 3.92 (dd, 1H), 3.44 (s, 3H), 2.74-2.79 (m, 2H), 2.56-2.60 (m, 2H), 2.21-2.26 (m, 1H), 1.94-1.99 (m, 1H). LCMS (Method D): RT=0.79 min, M+H+=430.2.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-21e968542a6e4934be0b7e6a94203c27
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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