Hydrochloric Acid → 2-[(5-Chloro-2-{[3-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide

HRID 1864040Notes

Reaction equation

HRID 1864040 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=2[C:11]([NH:13][CH:14]([CH3:16])[CH3:15])=[O:12])[C:5]([Cl:21])=[CH:4][N:3]=1.[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:30]=[C:31]([CH:33]=[CH:34][CH:35]=2)[NH2:32])[CH2:25][CH2:24]1.Cl>C(O)(C)C>[Cl:21][C:5]1[C:6]([NH:8][C:9]2[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=2[C:11]([NH:13][CH:14]([CH3:16])[CH3:15])=[O:12])=[N:7][C:2]([NH:32][C:31]2[CH:33]=[CH:34][CH:35]=[C:29]([N:26]3[CH2:25][CH2:24][N:23]([CH3:22])[CH2:28][CH2:27]3)[CH:30]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 115646133-(4-Methylpiperazin-1-yl)anilineHCID 579742032-[(2,5-dichloro-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide

Product 1

HCID 579742232-[(5-Chloro-2-{[3-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamideYield 41%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
95 °C

Procedure

2-[(2,5-Dichloro-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide (200 mg, 0.61 mmol) and 3-(4-methyl-1-piperazinyl)aniline (117 mg, 0.61 mmol) were combined in a vessel with 8 mL isopropanol and 12N HCl (51 μL, 0.61 mmol). The vessel was sealed and heated with stirring at 95° C. for 18 h. The reaction was cooled to room temperature and the solid was filtered off and washed with diethyl ether to give 120 mg (40%) of an off-white solid as the HCl salt. Mass (M+H)+=480, 481, 482.

Workup

  1. customThe vessel was sealed
  2. temperatureheated
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationthe solid was filtered off
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-fca6a2c1741649219e2d01691e249297
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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