N,N-Dimethylethylenediamine → HCID 57448661, compound

HRID 1669935Notes

Reaction equation

HRID 1669935 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:21]([NH:22][C:23]3[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([O:31][CH3:32])[CH:24]=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.[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36][NH2:37]>CN(C=O)C>[CH3:32][O:31][C:25]1[CH:24]=[C:23]([NH:22][C:21]2[C:12]([NH:11][S:8]([C:5]3[CH:6]=[N:7][C:2]([NH:37][CH2:36][CH2:35][N:34]([CH3:38])[CH3:33])=[CH:3][CH:4]=3)(=[O:10])=[O:9])=[N:13][C:14]3[C:19]([N:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 16045611HCID 16045611, compound

Product 1

HCID 57448661HCID 57448661, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

6-chloro-N-(3-(3,5-dimethoxyphenylamino)quinoxalin-2-yl)-pyridine-3-sulfonamide (100 mg, 0.21 mmol), prepared using procedures similar to those used in Example 8, KHCO3 (40 mg, 0.40 mmol), N1,N1-dimethylethane-1,2-diamine (225 μL, 2.0 mmol) and dry DMF (1.0 mL) were combined and heated to 130° C. with stirring overnight. The reaction mixture was concentrated in vacuo and purified by preparative HPLC to give N-(3-(3,5-dimethoxy-phenylamino)-quinoxalin-2-yl)-6-(2-(dimethylamino)ethylamino)pyridine-3-sulfonamide (21.0 mg, 19%). 1H NMR (400 MHz, DMSO-d6) δ 8.76 (br s, 1H), 8.63 (d, 1H), 8.07 (dd, 1H), 7.40 (m, 1H), 7.34 (m, 1H), 7.28 (d, 2H), 7.14 (m, 4H), 6.47 (d, 1H), 6.12 (m, 1H), 3.75 (s, 6H), 3.35 (m, 2H), 3.14 (m, 2H), 2.74 (s, 6H). MS (EI) m/z for C25H29N7O4S: 524.1 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-fe1fcddf351f40a185aff30b804cdd1d
Source dataset
uspto-grants-2011_08
Patent number
US07989622B2

Reaction notes

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