Succinic anhydride → HCID 24999764, compound

HRID 424141Notes

Reaction equation

HRID 424141 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

HCID 7922Succinic anhydrideHCID 24829325HCID 24829325, compound

Product 1

HCID 24999764HCID 24999764, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was triturated with hexanes
  3. filtrationThe resulting white powder was filtered
  4. washwashed with hexanes
  5. dissolutionThe solids were re-dissolved in EtOAc
  6. washwashed with sat. aqueous ammonium chloride solution (2×15 mL)
  7. dry with materialdried (NaSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-597d3ff3e41e463cab4b8fc519354fd0
Source dataset
uspto-grants-2012_01
Patent number
US08101773B2

Reaction notes

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