(Diethylamino)sulfur trifluoride → HCID 44555668, compound

HRID 43006Notes

Reaction equation

HRID 43006 reaction equation
O[CH2:2][C:3]1[C:4]([C:25]([F:28])([F:27])[F:26])=[N:5][N:6]([CH2:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[CH2:14][C@H:13]([NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH2:12]3)[CH:7]=1.CCN(S(F)(F)[F:35])CC>C(Cl)Cl>[F:35][CH2:2][C:3]1[C:4]([C:25]([F:28])([F:27])[F:26])=[N:5][N:6]([CH2:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[CH2:14][C@H:13]([NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH2:12]3)[CH:7]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 44556366HCID 44556366, compound

Product 1

HCID 44555668HCID 44555668, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)—N-(5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide (6.0 mg, 14 μmol) in DCM (3 mL) was added DAST (0.3 mL, 14 μmol). The whole was stirred at room temperature overnight before the reaction mixture was quenched by the addition of water (2 mL). The organics were filtered through a hydrophobic frit before being concentrated to dryness and the residue purified by basic preparative HPLC to give the title compound (1.0 mg, 2.4 μmol, 17%). MS (ESI): m/z [M−H]− 418.0

Workup

  1. customwas quenched by the addition of water (2 mL)
  2. filtrationThe organics were filtered through a hydrophobic frit
  3. concentrationbefore being concentrated to dryness
  4. customthe residue purified by basic preparative HPLC

Sources & evidence

ORD record
ord-6ef06fd05ef34fb7a76200c2e3e3a873
Source dataset
uspto-grants-2013_09
Patent number
US08536214B2

Reaction notes

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