Succinic anhydride → HCID 24999764, compound
Reaction equation
C(C1C=C([CH2+]=NC2C=CC(OC3C=CN=C(C(NC)=O)C=3)=CC=2F)N(C2C=CC=C(CO)C=2)N=1)(C)(C)C.[C:38]([C:42]1[CH:46]=[C:45]([NH:47][C:48]([NH:50][C:51]2[CH:67]=[CH:66][C:54]([O:55][C:56]3[CH:61]=[CH:60][N:59]=[C:58]([C:62]([NH:64][CH3:65])=[O:63])[CH:57]=3)=[CH:53][C:52]=2[F:68])=[O:49])[N:44]([C:69]2[CH:74]=[CH:73][CH:72]=[C:71]([CH2:75][OH:76])[CH:70]=2)[N:43]=1)([CH3:41])([CH3:40])[CH3:39].[C:77]1(=[O:83])[O:82][C:80](=[O:81])[CH2:79][CH2:78]1>O1CCCC1>[C:38]([C:42]1[CH:46]=[C:45]([NH:47][C:48](=[O:49])[NH:50][C:51]2[CH:67]=[CH:66][C:54]([O:55][C:56]3[CH:61]=[CH:60][N:59]=[C:58]([C:62](=[O:63])[NH:64][CH3:65])[CH:57]=3)=[CH:53][C:52]=2[F:68])[N:44]([C:69]2[CH:70]=[C:71]([CH:72]=[CH:73][CH:74]=2)[CH2:75][O:76][C:77](=[O:83])[CH2:78][CH2:79][C:80]([OH:82])=[O:81])[N:43]=1)([CH3:41])([CH3:39])[CH3:40]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a room temperature solution of example 1, (4-{4-[({3-tert-butyl-1-[3-(hydroxymethyl)phenyl]-1H-pyrazol-5-yl}carbamoyl)amino]-3-fluorophenoxy}-N-methylpyridine-2-carboxamide, (0.45 g, 0.85 mmol) in tetrahydrofuran (43 mL) was added succinic anhydride (0.10 g, 1.00 mmol). The reaction mixture was allowed at stir at room temperature for 72 h. The reaction mixture was concentrated and the residue was triturated with hexanes. The resulting white powder was filtered and washed with hexanes. The solids were re-dissolved in EtOAc, washed with sat. aqueous ammonium chloride solution (2×15 mL), dried (NaSO4) and concentrated to afford 0.49 g (91%) of pure product. MS m/z 633.1 (M+H)+; Retention time (LC-MS): 3.29 min.