1,1-Dimethoxyethyl(dimethyl)amine → 1-(4-Fluorobenzyl)-5-methanesulfonyl-2-(3-methyl-[1,2,4]oxadiazol-5-yl)indole

HRID 1814100Notes

Reaction equation

HRID 1814100 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:20]([NH2:22])=[O:21])=[CH:4][CH:3]=1.CO[C:27](OC)([N:29](C)C)[CH3:28]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:20]2[O:21][N:29]=[C:27]([CH3:28])[N:22]=2)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 225043691-(4-Fluorobenzyl)-5-methanesulfonylindole-2-carboxamide

Product 1

HCID 120945531-(4-Fluorobenzyl)-5-methanesulfonyl-2-(3-methyl-[1,2,4]oxadiazol-5-yl)indole

Conditions

Temperature
110 °C

Procedure

A mixture of 1-(4-fluorobenzyl)-5-methanesulfonylindole-2-carboxamide (63 mg) and dimethylacetamide dimethylacetal (1 ml) was stirred at 110° C. for 1 hour. The reaction mixture was concentrated under reduced pressure. A mixture of the resulting residue, hydroxylamine hydrochloride (25 mg), a 2N aqueous sodium hydroxide solution (0.18 ml), 1,4-dioxane (0.4 ml) and acetic acid (0.4 ml) was stirred at 90° C. for 2 hours. Water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 50 mg of the desired product as a white crystal.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionA mixture of the resulting residue, hydroxylamine hydrochloride (25 mg)
  3. stirringa 2N aqueous sodium hydroxide solution (0.18 ml), 1,4-dioxane (0.4 ml) and acetic acid (0.4 ml) was stirred at 90° C. for 2 hours
  4. additionWater was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-89192e409dbb4128a0dfdd7d17f223aa
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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