Cesium carbonate → HCID 59837591, compound

HRID 273499Notes

Reaction equation

HRID 273499 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:20]=[C:19]([CH3:21])[C:13]2[N:14]=[C:15]([NH2:18])[N:16]=[N:17][C:12]=2[CH:11]=1.Br[C:23]1[CH:24]=[C:25]([S:29]([NH:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:20]=[C:19]([CH3:21])[C:13]2[N:14]=[C:15]([NH:18][C:23]3[CH:24]=[C:25]([S:29]([NH:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])(=[O:30])=[O:31])[CH:26]=[CH:27][CH:28]=3)[N:16]=[N:17][C:12]=2[CH:11]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 38617893-bromo-N-(2-(dimethylamino)ethyl)benzenesulfonamideHCID 248227537-(2-Chloro-5-methoxyphenyl)-5-methylbenzo[e][1,2,4]triazin-3-amine

Product 1

HCID 59837591HCID 59837591, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine (0.333 mmol, 1.0 equiv), 3-bromo-N-(2-dimethylamino-ethyl)-benzenesulfonamide (0.499 mmol, 1.5 equiv), Cs2CO3 (0.999 mmol, 3.0 equiv), Pd2(dba)3 (0.0333 mmol, 0.1 equiv), and Xantphos (0.0666 mmol, 0.2 equiv) were dissolved in 7 mL dioxane. The reaction was placed under an argon atmosphere and refluxed at 100° C. for 18 h. The organics were filtered to remove excess inorganics, dissolved in EtOAc, washed with saturated NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-[7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-(2-dimethylamino-ethyl)-benzenesulfonamide, which was precipitated using EtOAc/hexanes (1:5 v/v) to give a dark orange solid (168.4 mg, 96% yield). Rf=0.50 MS (ES+) m/z=527.

Workup

  1. filtrationThe organics were filtered
  2. customto remove excess inorganics
  3. dissolutiondissolved in EtOAc
  4. washwashed with saturated NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-077af60ea1f4444cad3493ecebaa34db
Source dataset
uspto-grants-2008_11
Patent number
US07456176B2

Reaction notes

Loading…