1-Methylpiperazine → 4-(4-Methyl-piperazin-1-ylmethyl)-N-[4-methyl-3-(2-pyridin-4-yl-6-(trifluoromethyl)pyrimidin-4-ylamino)-phenyl]benzamide

HRID 2084190Notes

Reaction equation

HRID 2084190 reaction equation
Cl[CH2:2][C:3]1[CH:35]=[CH:34][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([NH:17][C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[N:21]=[C:20]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[N:19]=3)[CH:11]=2)=[O:8])=[CH:5][CH:4]=1.[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH3:36][N:37]1[CH2:42][CH2:41][N:40]([CH2:2][C:3]2[CH:35]=[CH:34][C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([NH:17][C:18]4[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[N:21]=[C:20]([C:28]5[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=5)[N:19]=4)[CH:11]=3)=[O:8])=[CH:5][CH:4]=2)[CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 227323644-chloromethyl-N-[4-methyl-3-(2-pyridin-4-yl-6-(trifluoromethyl)pyrimidin-4-ylamino)-phenyl]benzamide

Product 1

HCID 227323494-(4-Methyl-piperazin-1-ylmethyl)-N-[4-methyl-3-(2-pyridin-4-yl-6-(trifluoromethyl)pyrimidin-4-ylamino)-phenyl]benzamideYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring mixture of 4-chloromethyl-N-[4-methyl-3-(2-pyridin-4-yl-6-(trifluoromethyl)pyrimidin-4-ylamino)-phenyl]benzamide (48 mg, 0.096 mmol) and 1-methylpiperazine (16 μl, 0.0.144 mmol) in anhydrous tetrahydrofuran (5 ml) was added N,N-diisopropylethylamine (200 μl). The mixture was refluxed for 20 h. The mixture was cooled to room temperature and then rotary evaporated to dryness. The residue was purified by column chromatography and isolated as a tan solid (22 mg, 41%). 1H NMR (CDCl3): 8.77 (dd, J=1.8, 4.5 Hz, 2H), 8.29 (dd, J=1.5, 4.5 Hz, 2H), 8.01 (s, 1H), 7.85 (s, 1H), 7.83 (d, J=8.1 Hz, 2H), 7.47 (d, J=7.8 Hz, 2H), 7.37 (dd, J=1.5, 8.4 Hz, 1H), 7.33 (d, J=8.4 Hz, 1H), 7.04 (s, 1H), 6.74 (s, 1H), 3.57 (s, 2H), 2.47 (s, 8H), 2.29 (s, 6H).

Workup

  1. temperatureThe mixture was refluxed for 20 h
  2. customrotary evaporated to dryness
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8c902b094153445cbdbbfadede631513
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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