ethyl 5-{[(6-amino-2,3-dihydro-1H-inden-5-yl)oxy]methyl}pyrazine-2-carboxylate trihydrochloride → ethyl 5-{[(6-{[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino}-2,3-dihydro-1H-inden-5-yl)oxy]methyl}pyrazine-2-carboxylate

HRID 1879398Notes

Reaction equation

HRID 1879398 reaction equation
Cl.Cl.Cl.[NH2:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][C:6]=1[O:14][CH2:15][C:16]1[N:17]=[CH:18][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:20][CH:21]=1.[CH3:27][C:28]1[N:29]=[C:30]([S:33](Cl)(=[O:35])=[O:34])[S:31][CH:32]=1.COC(C)(C)C>N1C=CC=CC=1>[CH3:27][C:28]1[N:29]=[C:30]([S:33]([NH:4][C:5]2[CH:13]=[C:12]3[C:8]([CH2:9][CH2:10][CH2:11]3)=[CH:7][C:6]=2[O:14][CH2:15][C:16]2[N:17]=[CH:18][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:20][CH:21]=2)(=[O:35])=[O:34])[S:31][CH:32]=1

Participants

4

Reactant 2

HCID 67106209ethyl 5-{[(6-amino-2,3-dihydro-1H-inden-5-yl)oxy]methyl}pyrazine-2-carboxylate trihydrochlorideHCID 866565784-Methyl-1,3-thiazole-2-sulfonylchloride tert-butyl methyl ether

Product 1

HCID 58398423ethyl 5-{[(6-{[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino}-2,3-dihydro-1H-inden-5-yl)oxy]methyl}pyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 712 mg of ethyl 5-{[(6-amino-2,3-dihydro-1H-inden-5-yl)oxy]methyl}pyrazine-2-carboxylate trihydrochloride were added 35.6 mL of pyridine and 35.0 mL of a 0.21 M 4-methyl-1,3-thiazole-2-sulfonyl chloride/tert-butyl methyl ether solution, followed by stirring overnight at room temperature. The reaction liquid was concentrated under reduced pressure, and to the obtained residue was added a 5% w/v aqueous citric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:1 to 95:5) to obtain 256 mg of ethyl 5-{[(6-{[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino}-2,3-dihydro-1H-inden-5-yl)oxy]methyl}pyrazine-2-carboxylate.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. additionto the obtained residue was added a 5% w/v aqueous citric acid solution
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:1 to 95:5)

Sources & evidence

ORD record
ord-59de3b2eeee648909b6a49530166ff4e
Source dataset
uspto-grants-2012_11
Patent number
US08314240B2

Reaction notes

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