Reaction #2358562

ord-739a2299047c422ebda932543ddb1fed

Reaction equation

CC1CC(C)CN(S(=O)(=O)c2ccc3c(c2)c(=S)c2cc(S(=O)(=O)N4CC(C)CC(C)C4)ccc2n3C)C1
2,7-bis(3,5-dimethylpiperidin-1-ylsulfonyl)-10-methylacridine-9(10H) thione
CN(C)CCCN
dimethylaminopropylamine
→
CC1CC(C)CN(S(=O)(=O)c2ccc3c(c2)c(=NCCCN(C)C)c2cc(S(=O)(=O)N4CC(C)CC(C)C4)ccc2n3C)C1
title compound
Yield 85.1%
CC1CC(C)CN(S(=O)(=O)c2ccc3c(c2)c(=NCCCN(C)C)c2cc(S(=O)(=O)N4CC(C)CC(C)C4)ccc2n3C)C1
2,7-bis(3,5-dimethylpiperidin-1-ylsulfonyl)-9-(3-dimethylaminopropyl)imino-10-methyl-(9H,10H)-acridine
Yield 85.1%

Reactants

CC1CC(C)CN(S(=O)(=O)c2ccc3c(c2)c(=S)c2cc(S(=O)(=O)N4CC(C)CC(C)C4)ccc2n3C)C1
2,7-bis(3,5-dimethylpiperidin-1-ylsulfonyl)-10-methylacridine-9(10H) thione
CN(C)CCCN
dimethylaminopropylamine

Reagents

None

Solvents

c1ccncc1
pyridine

Conditions

Temperature
100°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherSolvent was partially evaporated
  2. 2
    Otherreaction product
  3. 3
    Otherwas precipitated by addition of methanol
  4. 4
    FiltrationPrecipitate was collected by filtration
  5. 5
    Washwashed with methanol
  6. 6
    Otherdried

Procedure

A mixture of 2,7-bis(3,5-dimethylpiperidin-1-ylsulfonyl)-10-methylacridine-9(10H) thione (145 mg, 0.25 mmole), pyridine (5 mL) and dimethylaminopropylamine (0.125 mL, 1 mmole) was stirred at 100° C. for 4 hrs. Solvent was partially evaporated and reaction product was precipitated by addition of methanol. Precipitate was collected by filtration, washed with methanol and dried to give 137 mg (85%) of the title compound. MS 644 (MH+).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09120754B2uspto-grants-2015_09