Hydrochloric Acid → ethyl 5-(2-methoxyethoxy)-7-{[(1-methyl-1H-imidazol-2-yl)sulfonyl]amino}-1H-indole-2-carboxylate

HRID 1994849Notes

Reaction equation

HRID 1994849 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:16][CH2:17][CH2:18][O:19][CH3:20])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.N1C(C)=CC=CC=1C.[CH3:29][N:30]1[CH:34]=[CH:33][N:32]=[C:31]1[S:35](Cl)(=[O:37])=[O:36].Cl>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH3:20][O:19][CH2:18][CH2:17][O:16][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([NH:1][S:35]([C:31]3[N:30]([CH3:29])[CH:34]=[CH:33][N:32]=3)(=[O:37])=[O:36])[CH:3]=1)[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 116583831-Methyl-1H-imidazole-2-sulfonyl chlorideHCID 57476192ethyl 7-amino-5-(2-methoxyethoxy)-1H-indole-2-carboxylate

Product 1

HCID 59136127ethyl 5-(2-methoxyethoxy)-7-{[(1-methyl-1H-imidazol-2-yl)sulfonyl]amino}-1H-indole-2-carboxylateYield 51.4%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 7-amino-5-(2-methoxyethoxy)-1H-indole-2-carboxylate (1 g) was dissolved in tetrahydrofuran (10 mL), then 2,6-lutidine (2.5 mL) and 1-methyl-1H-imidazole-2-sulfonyl chloride (0.98 g) were added under ice-cooling, and the mixture was stirred at room temperature for 2 hr. 1N Hydrochloric acid was added to the reaction solution under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over magnesium sulfate, and filtrated, and the filtrate was concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=10:90-100:0) to give the title compound (780 mg, yield 51%) as a white solid. MS: 566 (MH+).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltrated
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained crude product

Sources & evidence

ORD record
ord-cb0f449966f34ea18135d3ec02aa25b5
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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