Acetic Acid → HCID 67513150, compound

HRID 339716Notes

Reaction equation

HRID 339716 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[C:22]([NH:23][C:24]3[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:32][CH3:33])[C:25]=3[O:34][CH2:35][CH2:36][CH2:37][OH:38])=[N:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[C:39](O)(=[O:41])[CH3:40].O>CN(C=O)C>[OH:38][CH2:37][CH2:36][CH2:35][O:34][C:25]1[C:26]([O:32][CH3:33])=[CH:27][C:28]([O:30][CH3:31])=[CH:29][C:24]=1[NH:23][C:22]1[C:13]([NH:12][S:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][NH:1][C:39](=[O:41])[CH3:40])=[CH:4][CH:5]=2)(=[O:11])=[O:10])=[N:14][C:15]2[C:20]([N:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 67512675HCID 67512675, compound

Product 1

HCID 67513150HCID 67513150, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg of 4-aminomethyl-N-{3-[2-(3-hydroxypropoxy)-3,5-dimethoxyphenylamino]-quinoxalin-2-yl}benzenesulfonamide (content 82%), 37 mg of DAPECI and 8.7 l of acetic acid in 1 ml of DMF are stirred at RT overnight in a screw-cap vial. The reaction solution is poured into water, and the deposited precipitate is filtered off with suction. Purification by preparative HPLC on silica gel RP18 (acetonitrile, water) gives a total of 39 mg of N-(4-{3-[2-(3-hydroxypropoxy)-3,5-dimethoxyphenylamino]quinoxalin-2-ylsulfamoyl}benzyl)acetamide (yield 41%); MS-FAB (M+H+)=582.2; Rf (polar method): 2.19 min.

Workup

  1. filtrationthe deposited precipitate is filtered off with suction
  2. customPurification by preparative HPLC on silica gel RP18 (acetonitrile, water)

Sources & evidence

ORD record
ord-f2007c8a98f44f77a36ba45835f931f2
Source dataset
uspto-grants-2014_11
Patent number
US08895559B2

Reaction notes

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