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

HRID 1362853Notes

Reaction equation

HRID 1362853 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][CH2:14][CH2:15][OH:16])=[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][CH2:14][CH2:15][OH:16])=[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 579742162-[(2,5-Dichloro-4-pyrimidinyl)amino]-N-(2-hydroxyethyl)benzamide

Product 1

HCID 579742092-[(5-Chloro-2-{[3-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)amino]-N-(2-hydroxyethyl)benzamideYield 84.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
95 °C

Procedure

2-[(2,5-Dichloro-4-pyrimidinyl)amino]-N-(2-hydroxyethyl)benzamide (150 mg, 0.45 mmol) and 3-(4-methyl-1-piperazinyl)aniline (87 mg, 0.45 mmol) were combined in a vessel with 8 mL isopropanol and 12N HCl (38 μL, 0.45 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 ether to give 184 mg (76%) of an off-white solid as the HCl salt. Mass (M+H)+=482, 484.

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 ether

Sources & evidence

ORD record
ord-a0db47e6ca6d4b499fc2be0aaa2946db
Source dataset
uspto-grants-2011_02
Patent number
US07884098B2

Reaction notes

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