HCID 56967177, compound → HCID 67512675, compound

HRID 339715Notes

Reaction equation

HRID 339715 reaction equation
[C:1]([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)#[N:2]>C1COCC1.N.[Ni]>[NH2:2][CH2:1][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

Participants

5

Reactant 1

HCID 56967177HCID 56967177, compound

Product 1

HCID 67512675HCID 67512675, compoundYield 70.7%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.15 g of 4-cyano-N-{3-[2-(3-hydroxypropoxy)-3,5-dimethoxyphenylamino]quinoxalin-2-yl}-benzenesulfonamide in 5 ml of THF and 12 ml of methanolic ammonia solution (10%) are hydrogenated in a suitable pressure apparatus in the presence of 1.00 g of sponge nickel catalyst (Johnson-Matthey) at 50° C. and 5 bar for 17 hours. The catalyst is filtered off, rinsed with copious MeOH and THF, and the entire filtrate is evaporated, giving 819 mg of 4-aminomethyl-N-{3-[2-(3-hydroxypropoxy)-3,5-dimethoxyphenylamino]quinoxalin-2-yl}-benzenesulfonamide having a content of 82.4% (yield 59.4%); MS-FAB (M+H+)=540.2; Rf (polar method): 1.75 min.

Workup

  1. filtrationThe catalyst is filtered off
  2. washrinsed with copious MeOH and THF
  3. customthe entire filtrate is evaporated

Sources & evidence

ORD record
ord-4e4a883500134dadbffadf8eb1ee6965
Source dataset
uspto-grants-2014_11
Patent number
US08895559B2

Reaction notes

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