HCID 53262182, compound → HCID 53262413, compound

HRID 1509215Notes

Reaction equation

HRID 1509215 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:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)=[CH:52][C:53]4[NH:58][C:57](=[O:59])[CH:56]([CH3:60])[O:55][C:54]=4[N:61]=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:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)=[CH:52][C:53]4[NH:58][C:57](=[O:59])[CH:56]([CH3:60])[O:55][C:54]=4[N:61]=3)=[CH:48][CH:49]=2)[CH2:41][CH2:42][CH2:43]1

Participants

3

Reactant 2

HCID 53262182HCID 53262182, compoundHCID 67255234HCID 67255234, compound

Product 1

HCID 53262413HCID 53262413, compoundYield 94.1%

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-methyl-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (25 mg, 0.051 mmol) was reacted to afford the title compound (18.5 mg). 1H NMR (500 MHz, CD3OD): 7.37-7.42 (m, 4H), 7.34 (s, 1H), 7.28-7.30 (m, 3H), 7.18-7.20 (m, 2H), 5.03 (q, 1H), 2.73-2.79 (m, 2H), 2.56-2.60 (m, 2H), 2.20-2.26 (m, 1H), 1.96-1.99 (m, 1H), 1.65 (d, 3H). LCMS (Method D): RT=0.73 min, M+H+=386.2

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-8e108b5c6927467096c6a9aa6645ec3b
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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