Methyl iodide → 7-[4-(4-Chloro-phenyl)-piperazin-1-ylmethyl]-2-methyl-1,3,4,10a-tetrahydro-2H,9H-2,4-a,5,9-tetraaza-phenanthren-10-one

HRID 69677Notes

Reaction equation

HRID 69677 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:28]=[C:27]4[C:18]([N:19]5[CH:24]([C:25](=[O:29])[NH:26]4)[CH2:23][NH:22][CH2:21][CH2:20]5)=[N:17][CH:16]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:30](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][C:15]3[CH:28]=[C:27]4[C:18]([N:19]5[CH:24]([C:25](=[O:29])[NH:26]4)[CH2:23][N:22]([CH3:30])[CH2:21][CH2:20]5)=[N:17][CH:16]=3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 583244517-[4-(4-Chloro-phenyl)-piperazin-1-ylmethyl]-1,3,4,10a-tetrahydro-2H,9H-2,4a,5,9-tetraaza-phenanthren-10-one

Product 1

HCID 583244617-[4-(4-Chloro-phenyl)-piperazin-1-ylmethyl]-2-methyl-1,3,4,10a-tetrahydro-2H,9H-2,4-a,5,9-tetraaza-phenanthren-10-oneYield 3.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-[4-(4-Chloro-phenyl)-piperazin-1-ylmethyl]-1,3,4,10a-tetrahydro-2H,9H-2,4a,5,9-tetraaza-phenanthren-10-one (139 mg, 0.337 mmol) in DMF (3.4 mL) cooled to 0° C. was added potassium carbonate (233 mg, 1.683 mmol) and methyl iodide (2 M in THF, 0.168 mL). The reaction was stirred 1 h at 0° C. and filtered through celite. The filtrate was purified via HPLC (55-90% acetonitrile in water, ammonium bicarbonate buffer). The fractions were combined and concentrated until a white solid precipitated. The precipitate was filtered off and dried in vacuum to afford the title compound (4.6 mg, 3.2%) as a white solid. 1H NMR (DMSO-d6) δ (ppm): 10.59 (s, 1H), 7.68 (d, J=1.8 Hz, 1H), 7.15-7.28 (m, 2H), 7.01 (d, J=2.0 Hz, 1H), 6.85-6.97 (m, 2H), 4.17-4.30 (m, 1H), 3.88 (dd, J=10.6, 3.3 Hz, 1H), 3.37 (s, 2H), 3.14-3.20 (m, 1H), 3.06-3.14 (m, 4H), 2.84 (d, J=11.6 Hz, 1H), 2.74 (td, J=12.4, 3.0 Hz, 1H), 2.44-2.48 (m, 4H), 2.26 (s, 3H), 1.91-2.02 (m, 2H). [M+H] calc'd for C22H27ClN6O, 427; found, 427.

Workup

  1. filtrationfiltered through celite
  2. customThe filtrate was purified via HPLC (55-90% acetonitrile in water, ammonium bicarbonate buffer)
  3. concentrationconcentrated until a white solid
  4. customprecipitated
  5. filtrationThe precipitate was filtered off
  6. customdried in vacuum

Sources & evidence

ORD record
ord-79a8185d74e54569b0c7b7dd5013086d
Source dataset
uspto-grants-2014_09
Patent number
US08822470B2

Reaction notes

Loading…