Toluene → HCID 16045611, compound

HRID 336789Notes

Reaction equation

HRID 336789 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:21](Cl)=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:29]=[C:30]([O:32][CH3:33])[CH:31]=1)[NH2:28].C1(C)C=CC=CC=1>CCOCC>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:21]([NH:28][C:27]3[CH:29]=[C:30]([O:32][CH3:33])[CH:31]=[C:25]([O:24][CH3:23])[CH:26]=3)=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 663013,5-DimethoxyanilineHCID 57448734HCID 57448734, compound

Product 1

HCID 16045611HCID 16045611, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
125 °C

Procedure

6-Chloro-N-(3-chloroquinoxalin-2-yl)pyridine-3-sulfonamide (775 mg, 2.2 mmol), 3,5-dimethoxyaniline (355 mg, 2.3 mmol) and toluene (12 mL) were combined and heated to 125° C. with stirring overnight. The reaction was allowed to cool to room temperature and diluted with Et2O with vigorous stirring. The resulting solids were filtered, washed with Et2O and dried to give 6-chloro-N-(3-(3,5-dimethoxy-phenylamino)quinoxalin-2-yl)pyridine-3-sulfonamide (920 mg, 89%). 1H NMR (400 MHz, DMSO-d6) δ 12.20 (br s, 1H), 9.12 (d, 1H), 9.01 (br s, 1H), 8.53 (dd, 1H), 7.91 (br d, 1H), 7.77 (d, 1H), 7.60 (dd, 1H), 7.40 (m, 4H), 6.26 (m, 1H), 3.78 (s, 6H). MS (EI) m/z for C21H18ClN5O4S: 472.0 (MH+).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe resulting solids were filtered
  3. washwashed with Et2O
  4. customdried

Sources & evidence

ORD record
ord-826a97bb140b46a29ddc92f6b8292744
Source dataset
uspto-grants-2014_11
Patent number
US08889664B2

Reaction notes

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