Tetrahydrofuran → HCID 54256376, compound

HRID 1953291Notes

Reaction equation

HRID 1953291 reaction equation
Cl.[CH2:2]([O:4][C:5]([CH2:7][N:8]([S:29]([C:32]1[CH:33]=[CH:34][CH:35]=[C:36]2[C:41]=1[N:40]=[CH:39][CH:38]=[CH:37]2)(=[O:31])=[O:30])[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[C:13]([CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[NH:25])=[CH:22][CH:21]=1)=[CH:12]2)=[O:6])[CH3:3].[C:42](=[O:45])([O-])[O-:43].[K+].[K+].O1[CH2:52][CH2:51]CC1>>[CH2:2]([O:4][C:5]([CH2:7][N:8]([S:29]([C:32]1[CH:33]=[CH:34][CH:35]=[C:36]2[C:41]=1[N:40]=[CH:39][CH:38]=[CH:37]2)(=[O:30])=[O:31])[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[C:13]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([NH2:26])=[N:25][C:42]([O:43][CH2:51][CH2:52][S:29]([CH3:32])(=[O:31])=[O:30])=[O:45])=[CH:27][CH:28]=1)=[CH:12]2)=[O:6])[CH3:3]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 23302257HCID 23302257, compound

Product 1

HCID 54256376HCID 54256376, compound

Procedure

300 mg (0.5 mmol) of 4-[(5-(N-ethoxycarbonylmethyl-quinolin-8-yl-sulphonylamino)-1-methyl-indol-2-yl)-methyl]-benzamidine-hydrochloride, 170 mg (0.6 mmol) of 2-(methylsulphonyl)-ethyl-4-nitrophenylcarbonate and 210 mg (1.5 mmol) of potassium carbonate are stirred in 30 ml tetrahydrofuran for 5 hours at ambient temperature. Then the reaction mixture is filtered and the mother liquor is concentrated by evaporation. The residue is taken up in methylene chloride and washed with sodium hydrogen carbonate solution. The combined organic extracts are dried and concentrated by evaporation. The residue is chromatographed on aluminium oxide and eluted with methylene chloride/ethanol (99:1).

Workup

  1. filtrationThen the reaction mixture is filtered
  2. concentrationthe mother liquor is concentrated by evaporation
  3. washwashed with sodium hydrogen carbonate solution
  4. customThe combined organic extracts are dried
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed on aluminium oxide
  7. washeluted with methylene chloride/ethanol (99:1)

Sources & evidence

ORD record
ord-0fd4f96f39514bbfa9d5459779025476
Source dataset
uspto-grants-2000_09
Patent number
US06114532

Reaction notes

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