Hydrochloric Acid → N-[4-(5-Chloro-2-methyl-phenyl)-6-(4-trifluoromethyl-phenylamino)-pyrimidin-2-yl]-succinamic acid

HRID 28591Notes

Reaction equation

HRID 28591 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:32])=[C:6]([C:8]2[CH:13]=[C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[N:11]=[C:10]([N:25]3[C:29](=[O:30])[CH2:28][CH2:27][C:26]3=[O:31])[N:9]=2)[CH:7]=1.[O:33]1CCCC1.[OH-].[Na+].Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:32])=[C:6]([C:8]2[CH:13]=[C:12]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=3)[N:11]=[C:10]([NH:25][C:26](=[O:31])[CH2:27][CH2:28][C:29]([OH:30])=[O:33])[N:9]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 689846241-[4-(5-Chloro-2-methyl-phenyl)-6-(4-trifluoromethyl-phenylamino)-pyrimidin-2-yl]-pyrrolidine-2,5-dione

Product 1

HCID 11340555N-[4-(5-Chloro-2-methyl-phenyl)-6-(4-trifluoromethyl-phenylamino)-pyrimidin-2-yl]-succinamic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 1-[4-(5-chloro-2-methyl-phenyl)-6-(4-trifluoromethyl-phenylamino)-pyrimidin-2-yl]-pyrrolidine-2,5-dione (0.15 g, 0.33 mmol), tetrahydrofuran (15 ml), and water (15 ml), cooled in an ice bath, was added aqueous sodium hydroxide solution (0.25 M, 4.0 ml, 1.0 mmol) dropwise. After stirring for 1 hour, hydrochloric acid (0.25 M, 8.0 ml, 2.0 mmol) was added dropwise. Evaporation of the tetrahydrofuran under reduced pressure and filtration provided the title compound as hydrochloride salt (93% yield). 1H NMR (CD3OD) δ 2.48 (s, 3H, CH3), 2.73-2.76 (m, 2H, CH2), 2.89-2.92 (m, 2H, CH2), 6.81 (s, 1H, Ar), 7.45 (d, 1H, J=8.3 Hz, Ar), 7.54 (dd, 1H, J=8.3 Hz, J=2.2 Hz, Ar), 7.60 (d, 1H, J=2.2 Hz, Ar), 7.76 (d, 2H, J=8.6 Hz, Ar), 8.04 (d, 2H, J=7.9 Hz, Ar).

Workup

  1. customEvaporation of the tetrahydrofuran
  2. filtrationunder reduced pressure and filtration

Sources & evidence

ORD record
ord-dfdac2569fb948338d61c4cd647b18cd
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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