4-(4-Methylpiperazin-1-yl)aniline → HCID 178426332, compound

HRID 641050Notes

Reaction equation

HRID 641050 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][NH:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[C:12]([C:14]2[CH:22]=[C:21]3[C:17]([C:18](=[CH:24]O)[C:19](=[O:23])[NH:20]3)=[CH:16][CH:15]=2)=[O:13])=[CH:5][C:4]([CH3:29])=[N:3]1.[CH3:30][N:31]1[CH2:36][CH2:35][N:34]([C:37]2[CH:42]=[CH:41][C:40]([NH2:43])=[CH:39][CH:38]=2)[CH2:33][CH2:32]1>C1COCC1>[CH3:1][N:2]1[C:6]([CH2:7][NH:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[C:12]([C:14]2[CH:22]=[C:21]3[C:17](/[C:18](=[CH:24]/[NH:43][C:40]4[CH:39]=[CH:38][C:37]([N:34]5[CH2:33][CH2:32][N:31]([CH3:30])[CH2:36][CH2:35]5)=[CH:42][CH:41]=4)/[C:19](=[O:23])[NH:20]3)=[CH:16][CH:15]=2)=[O:13])=[CH:5][C:4]([CH3:29])=[N:3]1

Participants

4

Reactant 2

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 178426333HCID 178426333, compound

Product 1

HCID 178426332HCID 178426332, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 6-{3-[(2,5-Dimethyl-2H-pyrazol-3-ylmethyl)-amino]-benzoyl}-3-hydroxymethylene-1,3-dihydro-indol-2-one (prepared below, 0.045 g, 0.117 mmol) and THF (2 mL). To the resulting solution was added 4-(4-Methyl-piperazin-1-yl)-phenylamine (23 mg, 0.117 mmol), and the mixture was stirred for 24 h at 65° C. The reaction mixture was cooled to room temperature and the precipitate that formed was collected by filtration. The yellow solid was dissolved in 5 mL of a solvent mixture containing 98% EtOAc/2% i-prOH and washed with water (2×5 mL). The organic layers were combined, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude residue was columned over silica (95/5, chloroform/Hexanes w/0.5% NEt3 to afford the title compound in 39% yield (26 mg, 0.045 mmol).

Workup

  1. customA small screw cap test tube
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe precipitate that formed
  4. filtrationwas collected by filtration
  5. dissolutionThe yellow solid was dissolved in 5 mL of a solvent mixture
  6. additioncontaining 98% EtOAc/2% i-prOH
  7. washwashed with water (2×5 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-256bb2ff524b4c6abebf37b9c6351273
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

Loading…