Hydrochloric Acid → HCID 18704814, compound

HRID 343383Notes

Reaction equation

HRID 343383 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([O:10][CH3:11])=[N:8][C:7]([Br:12])=[CH:6][N:5]=1.[CH2:13]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24]([S:29](OC3C=CC([N+]([O-])=O)=CC=3)(=[O:31])=[O:30])=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:19][CH:18]=1)[CH:14]([CH3:16])[CH3:15].Cl>C(COC)OC.O>[Br:12][C:7]1[N:8]=[C:9]([O:10][CH3:11])[C:4]([NH:3][S:29]([C:24]2[C:23]([C:20]3[CH:19]=[CH:18][C:17]([CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:22][CH:21]=3)=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:31])=[O:30])=[N:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 113447242-Amino-5-bromo-3-methoxypyrazineHCID 187047924-Nitrophenyl 4'-isobutyl-2-biphenylsulphonate

Product 1

HCID 18704814HCID 18704814, compoundYield 24.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium hydride (60% dispersion in oil; 0.094 g) was added to a solution of 2-amino-5-bromo-3-methoxypyrazine (0.159 g) in dimethoxyethane (4 ml). The solution was stirred for 10 minutes and then 4-nitrophenyl 4'-isobutyl-2-biphenylsulphonate (0.321 g) was added. The solution was allowed to stand for 5 hours and then water (20 ml) was added. 2M Hydrochloric acid (2 ml) was added and the mixture was extracted with ethyl acetate (2×30 ml). The extracts were dried (MgSO4) and volatile material was removed by evaporation. The residue was purified by elution with ethyl acetate/hexane (1:3 v/v) through a silica gel Mega Bond Elut column. The resulting solid was recrystallised from a mixture of ether and hexane to give N-(5-bromo-3-methoxy-2-pyrazinyl)-4'-isobutyl-2-biphenylsulphonamide (0.09 g), m.p. 154°-156° C.; 1H NMR (d6 -DMSO): 0.9 (d,6H), 1.8-2.0 (m,1H), 2.5 (d,2H), 3.85 (s,3H), 7.1 (s,4H), 7.3 (d,1H), 7.5-7.7 (m,2H), 7.8 (br s,1H), 8.05 (d,1H), 10.2-10.3 (br, 1H); mass spectrum (+ve FAB, methanol/NBA): 478 (M+H)+.

Workup

  1. waitto stand for 5 hours
  2. extractionthe mixture was extracted with ethyl acetate (2×30 ml)
  3. dry with materialThe extracts were dried (MgSO4) and volatile material
  4. customwas removed by evaporation
  5. customThe residue was purified by elution with ethyl acetate/hexane (1:3 v/v) through a silica gel Mega Bond Elut column
  6. customThe resulting solid was recrystallised from a mixture of ether and hexane

Sources & evidence

ORD record
ord-eb5fd39db05d4d6ca69aa75cf74b7374
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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