4-Toluenesulfonyl chloride → HCID 15288312, compound

HRID 1463360Notes

Reaction equation

HRID 1463360 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[C:16]2[CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][N:28]([C:31]2[C:36]([O:37][CH3:38])=[CH:35][N:34]=[CH:33][N:32]=2)[CH2:27][CH2:26]1.C(N(CC)CC)C.C(Cl)Cl.CO>C1COCC1>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([NH:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[C:16]3[CH2:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][N:28]([C:31]3[C:36]([O:37][CH3:38])=[CH:35][N:34]=[CH:33][N:32]=3)[CH2:27][CH2:26]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chloride2×HCID 8471TriethylamineHCID 199620373-[3-[4-(5-Methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-amino-1H-indoleHCID 21226129Dichloromethane methanol

Product 1

HCID 15288312HCID 15288312, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

p-Toluenesulfonyl chloride (0.30 g, 1.56 mmol) was dissolved in 2 mL of THF, and the solution was cooled to 0° C. A mixture of 1-[3-[5-amino-1-H-indol-3-yl]propyl]-4-(5-methoxy-4-pyrimidinyl)piperazine (0.5 g, 1.42 mmol), and triethylamine (0.16 g, 1.56 mmol) in 3 mL of THF was added to the p-toluenesulfonyl chloride solution. The solution was stirred at 0° C. for 30 min, warmed to 23° C. (1 h), and concentrated in vacuo. Silica gel column chromatography (95:5:0.5 CH2Cl2 -MeOH-30% NH4OH) of the concentrate gave 1-[3-[5-[[(4-methylphenyl) sulfonyl]amino]-1-H-indol-3-yl]propyl]-4-(5-methoxy-4-pyrimidinyl)piperazine (0.42 g, 0.8 mmol, 57%). The free base (0.42 g, 0.80 mmol) was dissolved in a minimum volume of acetonitrile. A concentrated solution of oxalic acid (0.072 g, 0.8 mmol) in CH3CN was added with stirring. The precipitate was separated by filtration, washed sparingly with CH3CN and dried at 70° C. in vacuo overnight to give the title compound (0.40 g, 0.66 mmol, 82%): mp 125°-127° C. Anal. Calcd for C27H32N6O3S1.1.0 C2H2O4 : C, 55.40; H, 5.77; N, 13.36. Found: C, 55.29; H, 5.41; N, 13.15.

Workup

  1. temperaturewarmed to 23° C. (1 h)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-778c3b5d9f66455cbb15f3b950a9b0b0
Source dataset
uspto-grants-1994_04
Patent number
US05300506

Reaction notes

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