(Diethylamino)sulfur trifluoride → HCID 67060000, compound

HRID 238292Notes

Reaction equation

HRID 238292 reaction equation
O[C:2]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][N:5]([C:10]([C:12]1[CH:16]=[C:15]([C:17]3[CH:18]=[N:19][NH:20][CH:21]=3)[S:14][CH:13]=1)=[O:11])[CH2:6]2.C(N(S(F)(F)[F:34])CC)C>C(Cl)Cl>[F:34][C:2]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][N:5]([C:10]([C:12]1[CH:16]=[C:15]([C:17]3[CH:18]=[N:19][NH:20][CH:21]=3)[S:14][CH:13]=1)=[O:11])[CH2:6]2

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 51036948HCID 51036948, compound

Product 1

HCID 67060000HCID 67060000, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(8-Hydroxy-8-phenyl-3-aza-bicyclo[3.2.1]oct-3-yl)-[5-(1H-pyrazol-4-yl)-thiophen-3-yl]methanone (0.05 g, 0.12 mmol) in DCM (2 mL) was cooled to −78° C. under an atmosphere of nitrogen. Diethylaminosulphur trifluoride (0.05 mL) was added and the mixture stirred for 0.25 hour and allowed to warm to room temperature over 1 hour. The mixture was diluted with DCM and washed with water then dried over magnesium sulphate, filtered and the solvent removed by evaporation. The residue was purified by reverse phase HPLC and the fractions containing the desired products were combined and the solvent removed by lyophilisation to give the title compound as a white solid (0.02 g). LCMS m/z 382.1 [M+H]+. RT.=4.25 min (Analytical Method 2).

Workup

  1. washwashed with water
  2. dry with materialthen dried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent removed by evaporation
  5. customThe residue was purified by reverse phase HPLC
  6. additionthe fractions containing the desired products
  7. customthe solvent removed by lyophilisation

Sources & evidence

ORD record
ord-310ec003591b407ebd1ec4a8a82097b0
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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