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

HRID 1864054Notes

Reaction equation

HRID 1864054 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]([CH3:21])=[CH:4][N:3]=1.[NH2:22][C:23]1[CH:24]=[C:25]([N:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][C:30]2=[O:36])[CH:26]=[CH:27][CH:28]=1.Cl>C(O)(C)C>[CH3:15][CH:14]([NH:13][C:11](=[O:12])[C:10]1[CH:17]=[CH:18][CH:19]=[CH:20][C:9]=1[NH:8][C:6]1[C:5]([CH3:21])=[CH:4][N:3]=[C:2]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]3[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][C:30]3=[O:36])[CH:24]=2)[N:7]=1)[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 579741721-(3-Aminophenyl)-4-methylpiperazin-2-oneHCID 579742052-[(2-Chloro-5-methyl-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide

Product 1

HCID 24864097N-(1-methylethyl)-2-[(5-methyl-2-{[3-(4-methyl-2-oxo-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)amino]benzamideYield 27.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-[(2-Chloro-5-methyl-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide (103 mg, 0.337 mmol) and 1-(3-aminophenyl)-4-methyl-2-piperazinone (68.8 mg, 0.335 mmol) were stirred at 95° C. overnight in isopropanol (10 mL) with 12 N HCl (0.056 mL, 0.673 mmol). The reaction was cooled to room temperature and the solid was filtered off and washed with isopropanol. The solid was chromatographed using reverse phase HPLC eluting with 5-30% acetonitrile containing 0.1% formic acid to give a white solid (43 mg, 27%) after lyophilozation of the combined HPLC fractions. MS: M(C26H31N7O2)=473.57, (M+H)+=473.8.

Workup

  1. filtrationthe solid was filtered off
  2. washwashed with isopropanol
  3. customThe solid was chromatographed
  4. washeluting with 5-30% acetonitrile containing 0.1% formic acid

Sources & evidence

ORD record
ord-cbe5b2ce7a8e4f9280c3b985d18bc6fd
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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