Water → HCID 10578729, compound

HRID 343389Notes

Reaction equation

HRID 343389 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH3:9])=[N:6][C:5]([Br:10])=[CH:4][N:3]=1.[H-].[Na+].[CH2:13]([O:20][C:21]([N:23]([C:25]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:26]=1[CH:27]=[CH:28][CH:29]=[C:30]2[S:35](Cl)(=[O:37])=[O:36])[CH3:24])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>C(COC)OC>[CH2:13]([O:20][C:21]([N:23]([C:25]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:26]=1[CH:27]=[CH:28][CH:29]=[C:30]2[S:35]([NH:1][C:2]1[C:7]([O:8][CH3:9])=[N:6][C:5]([Br:10])=[CH:4][N:3]=1)(=[O:36])=[O:37])[CH3:24])=[O:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10572445HCID 10572445, compoundHCID 113447242-Amino-5-bromo-3-methoxypyrazine

Product 1

HCID 10578729HCID 10578729, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

2-Amino-5-bromo-3-methoxypyrazine (0.3 g) was added to a stirred suspension of sodium hydride (60% dispersion in oil; 0.15 g) in dimethoxyethane (5 ml). After 10 minutes, 5-(N-benzyloxycarbonyl-N-methylamino)-1-naphthalenesulphonyl chloride (0.6 g) in dimethoxyethane (2 ml) was added and stirring was continued for 2 hours. The mixture was poured into water (20 ml) and washed with ethyl acetate (20 ml). The aqueous layer was acidified with concentrated hydrochloric acid to pH2 and extracted with ethyl acetate (3×50 ml). The combined organic extracts were dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel (25 g), eluting with a gradient of 20-50% ethyl acetate in hexane to give 5-(N-benzyloxycarbonyl-N-methylamino)-N-(5-bromo-3-methoxy-2-pyrazinyl)-1-naphthalenesulphonamide (0.50 g) as a white foam; 1H NMR (d6 -DHSO): 3.34 (s,3H), 3.90 (s,3H), 5.08 (br,2H), 6.95 (br,1H), 7.19 (br,2H), 7.22-7.56 (m,2H), 7.6-7.77 (m,3H), 7.79 (s,1H), 8.07 (d,1H), 8.37 (dd,1H), 8.80 (d,1H), 11.58 (br,1H); mass spectrum (+ve FAB, DMSO/NBA): 557(M+H)+.

Workup

  1. waitwas continued for 2 hours
  2. washwashed with ethyl acetate (20 ml)
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (25 g)
  7. washeluting with a gradient of 20-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c310f742385d4767b60b15dc5096a03e
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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