Isovaleric Acid → HCID 44199928, compound
Reaction equation
[CH3:1][CH:2]([CH3:7])[CH2:3][C:4](O)=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:41][N:42]1[C:51]2[C:46](=[CH:47][N:48]=[C:49]([CH3:52])[CH:50]=2)[CH:45]=[C:44]([C:53]2[CH:54]=[C:55]([NH:60]/[C:61](/[NH2:64])=[N:62]/[OH:63])[CH:56]=[CH:57][C:58]=2[CH3:59])[C:43]1=[O:65]>CN(C=O)C>[CH2:3]([C:4]1[O:63][N:62]=[C:61]([NH:60][C:55]2[CH:56]=[CH:57][C:58]([CH3:59])=[C:53]([C:44]3[C:43](=[O:65])[N:42]([CH3:41])[C:51]4[C:46]([CH:45]=3)=[CH:47][N:48]=[C:49]([CH3:52])[CH:50]=4)[CH:54]=2)[N:64]=1)[CH:2]([CH3:7])[CH3:1]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
3-Methylbutanoic acid (13 mg, 0.12 mmol), HATU (50 mg, 0.12 mmol), and DIPEA (0.023 mL, 0.12 mmol) were stirred in dry DMF (3 mL) for 1 h before 17 (40 mg, 0.118 mmol) was added at rt. The stirring was continued for 1 h before it was heated at 100° C. for 5 h. After cooling and filtration, the mixture was purified by preparative LC/MS to give 3-(5-(5-isobutyl-1,2,4-oxadiazol-3-ylamino)-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one (A68) as a solid. 1H NMR (400 MHz, d4-MeOH) δ 8.92 (s, 1H), 7.92 (s, 1H), 7.73 (s, 1H), 7.33 (d, J=1 Hz, 1H), 7.24 (dd, J=8, 4 Hz, 1H), 7.14 (d, J=4 Hz, 1H), 3.72 (s, 3H), 2.72 (s, 3H), 2.60 (d, J=8 Hz, 2H), 2.10-2.01 (m, 1H), 2.06 (s, 3H), 0.92 (d, J=8 Hz, 6H). MS m/z 403.4, 404.5 (M+1).
Workup
- additionwas added at rt
- temperatureAfter cooling
- filtrationfiltration
- customthe mixture was purified by preparative LC/MS
Sources & evidence
- ORD record
- ord-bcaddde88d7b4b619495d00527cdb07f
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278452B2
Reaction notes
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