(Diethylamino)sulfur trifluoride → HCID 59571038, compound

HRID 2192940Notes

Reaction equation

HRID 2192940 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6](/[C:16](=[CH:26]\[C@H:27]3[CH2:31][CH2:30][CH:29](O)[CH2:28]3)/[C:17]([NH:19][C:20]3[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=3)=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH2:3][CH2:2]1.C(N(S(F)(F)[F:39])CC)C>ClCCl.O>[CH:1]1([C:4]2[CH:5]=[C:6](/[C:16](=[CH:26]\[C@H:27]3[CH2:31][CH2:30][CH:29]([F:39])[CH2:28]3)/[C:17]([NH:19][C:20]3[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=3)=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59571056HCID 59571056, compound

Product 1

HCID 59571038HCID 59571038, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2E)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(1S)-3-hydroxycyclopentyl]-N-(1-methyl-1H-pyrazol-3-yl)acrylamide (124 mg) in dichloromethane (4 ml) was added diethylaminosulfur trifluoride (100 μl) under ice-cooling, followed by stirring at room temperature for 15 minutes. The reaction mixture was diluted with dichloromethane, and water was added thereto. The organic layer was sequentially washed with saturated aqueous sodium bicarbonate and saturated brine, and dried over anhydrous magnesium sulfate. After concentrating under reduced pressure, the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=7:3-1:0) to obtain (2E)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(1S)-3-fluorocyclopentyl]-N-(1-methyl-1H-pyrazol-3-yl)acrylamide (78 mg) as a colorless amorphous substance.

Workup

  1. temperaturecooling
  2. additionwas added
  3. washThe organic layer was sequentially washed with saturated aqueous sodium bicarbonate and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationAfter concentrating under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=7:3-1:0)

Sources & evidence

ORD record
ord-10c9728a2f014e72939e14670c8a0ce3
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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