Sodium Sulfate → HCID 44200874, compound
Reaction equation
[F:1][C:2]([F:7])([CH3:6])[C:3](O)=[O:4].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.[O-]S([O-])(=O)=O.[Na+].[Na+].[CH3:48][N:49]1[C:58]2[C:53](=[CH:54][N:55]=[C:56]([CH3:59])[CH:57]=2)[CH:52]=[C:51]([C:60]2[CH:61]=[C:62]([NH:67]/[C:68](/[NH2:71])=[N:69]/O)[CH:63]=[CH:64][C:65]=2[CH3:66])[C:50]1=[O:72]>CN(C=O)C>[F:1][C:2]([C:3]1[O:4][N:69]=[C:68]([NH:67][C:62]2[CH:63]=[CH:64][C:65]([CH3:66])=[C:60]([C:51]3[C:50](=[O:72])[N:49]([CH3:48])[C:58]4[C:53]([CH:52]=3)=[CH:54][N:55]=[C:56]([CH3:59])[CH:57]=4)[CH:61]=2)[N:71]=1)([F:7])[CH3:6]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 2,2-difluoropropanoic acid (11 mg, 0.1 mmol), HATU (42 mg, 0.11 mmol) and DIPEA (15 mg, 0.12 mmol) in dry DMF (0.5 mL) at rt in the presence of anhydrous Na2SO4 (71 mg, 0.5 mmol) were added 17 (33.7 mg, 0.10 mmol) slowly. The consumption of 17 was determined to be completed by LC/MS. The mixture was heated at 100° C. for 2 h. Solid was filtered off and the residue was purified with preparative HPLC to yield 3-(5-(5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-ylamino)-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one (A54). 1H NMR (400 MHz, DMSO-d6) δ 10.27 (s, 1H), 9.00 (s, 1H), 8.03 (s, 1H), 7.70 (s, 1H), 7.42 (d, J=8.4 Hz, 1H), 7.33 (s, 1H), 7.27 (d, J=8.0 Hz, 1H), 2.70 (s, 3H), 2.51 (s, 3H), 2.16 (t, J=19.6 Hz, 3H), 2.10 (s, 3H). MS m/z 412.2 (M+1).
Workup
- customThe consumption of 17
- filtrationSolid was filtered off
- customthe residue was purified with preparative HPLC
Sources & evidence
- ORD record
- ord-cf39a84cda7344d6a95b864732a4905e
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278452B2
Reaction notes
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