Isobutyric Acid → HCID 44201108, compound
Reaction equation
[C:1]([OH:6])(=O)[CH:2]([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:40]([C:42]1[CH:51]=[C:50]2[C:45]([CH:46]=[C:47]([C:54]3[CH:55]=[C:56]([NH:61]/[C:62](/[NH2:65])=[N:63]/O)[CH:57]=[CH:58][C:59]=3[CH3:60])[C:48](=[O:53])[N:49]2[CH3:52])=[CH:44][N:43]=1)[CH3:41]>CN(C=O)C>[CH2:40]([C:42]1[CH:51]=[C:50]2[C:45]([CH:46]=[C:47]([C:54]3[CH:55]=[C:56]([NH:61][C:62]4[N:63]=[C:1]([CH:2]([CH3:4])[CH3:3])[O:6][N:65]=4)[CH:57]=[CH:58][C:59]=3[CH3:60])[C:48](=[O:53])[N:49]2[CH3:52])=[CH:44][N:43]=1)[CH3:41]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of isobutyric acid (8 μL, 0.09 mmol) in DMF (1 mL) were added DIPEA (16 μL, 0.09 mmol) and HATU (33 mg, 0.09 mmol). After stirring at rt for 15 min 17a (30 mg, 0.09 mmol) was added as a solution in DMF (0.5 mL). The reaction was stirred at rt until complete consumption of 17a was determined by LC/MS and then heated at 100° C. for 1 h. Subsequently the reaction was cooled to rt, filtered and purified by preparative LC/MS to give 7-ethyl-3-(5-(5-isopropyl-1,2,4-oxadiazol-3-ylamino)-2-methylphenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (A104). 1H NMR (400 MHz, d6-DMSO) δ 9.91 (s, 1H), 9.10 (s, 1H), 8.05 (s, 1H), 7.78 (s, 1H), 7.41 (dd, J=8, 2 Hz, 1H), 7.33 (d, J=2 Hz, 1H), 7.23 (d, J=8 Hz, 1H), 3.72 (s, 3H), 3.19 (m, 1H), 3.01 (q, J=7.6 Hz, 2H), 2.08 (s, 3H), 1.36 (t, J=7.6 Hz, 3H), 1.31, (d, J=6.8 Hz, 6H). MS m/z 404.1 (M+1).
Workup
- temperatureSubsequently the reaction was cooled to rt
- filtrationfiltered
- custompurified by preparative LC/MS
Sources & evidence
- ORD record
- ord-8b89f950de3a41d3980ffb9432eeaddd
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278452B2
Reaction notes
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