Hydrochloric Acid → HCID 57974201, compound

HRID 1864065Notes

Reaction equation

HRID 1864065 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]([F:20])=[CH:4][N:3]=1.[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:29]=[C:30]([CH:32]=[CH:33][CH:34]=2)[NH2:31])[CH2:24][CH2:23]1.C(O)C.Cl>O>[F:20][C:5]1[C:6]([NH:8][C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:7][C:2]([NH:31][C:30]2[CH:32]=[CH:33][CH:34]=[C:28]([N:25]3[CH2:24][CH2:23][N:22]([CH3:21])[CH2:27][CH2:26]3)[CH:29]=2)=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 115646133-(4-Methylpiperazin-1-yl)anilineHCID 57974155HCID 57974155, compound

Product 1

HCID 57974201HCID 57974201, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

Ethyl 2-[(2-chloro-5-fluoro-4-pyrimidinyl)amino]benzoate (1.0 g, 3.4 mmol), 3-(4-methyl-1-piperazinyl)aniline (0.65 g, 3.4 mmol), ethanol (45 mL) and 6N HCl (1.5 mL, 8.8 mmol) were heated with stirring in a reaction vessel, which was sealed and heated at 95° C. for 24 h. The reaction mixture was cooled to room temperature, poured into water, extracted with ethyl acetate and neutralized to pH 7 by the slow addition of 6N NaOH. The resulting precipitate was collected on a sintered glass funnel and washed with water and ethyl ether to afford the title compound as a tan solid; yield 1.0 g (65%). MS: M(C24H27FN6O2)=450.52 (M+H)+=451.2.

Workup

  1. customwhich was sealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate and neutralized to pH 7 by the slow addition of 6N NaOH
  4. customThe resulting precipitate was collected on a sintered glass funnel
  5. washwashed with water and ethyl ether

Sources & evidence

ORD record
ord-898d68333ce744fbbb6e2fbb7fb1139f
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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