(Diethylamino)sulfur trifluoride → HCID 71239245, compound

HRID 2171612Notes

Reaction equation

HRID 2171612 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([C:11]2[C@@H:12]([O:20][CH2:21][CH2:22][O:23][CH3:24])[C@@H:13]3[C@@H:18](O)[CH2:17][CH2:16][N:14]3[N:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].CCN(S(F)(F)[F:31])CC>C(Cl)Cl.O>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([C:11]2[C@@H:12]([O:20][CH2:21][CH2:22][O:23][CH3:24])[C@@H:13]3[C@H:18]([F:31])[CH2:17][CH2:16][N:14]3[N:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 71239426HCID 71239426, compound

Product 1

HCID 71239245HCID 71239245, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-chloro-4-((3S,3aS,4S)-4-hydroxy-3-(2-methoxyethoxy)-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile obtained in example 21 (400 mg, 1.14 mmol) in DCM (10 mL) at 0° C. was added DAST (0.18 mL, 1.34 mmol) and stirred at room temperature for 1 h. Once the starting material had disappeared (monitored by TLC), the reaction mixture was diluted with DCM, water and extracted, organic layer was washed with water, brine, dried over Na2SO4 and concentrated. Purification by column chromatography (silica gel, 30% EtOAc in Hexane) provided the title compound (215 mg, 53%).

Workup

  1. extractionextracted
  2. washorganic layer was washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography (silica gel, 30% EtOAc in Hexane)

Sources & evidence

ORD record
ord-5e910e3d79074a61befef0f8eb8b4418
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

Loading…