(Diethylamino)sulfur trifluoride → HCID 71239205, compound

HRID 2171605Notes

Reaction equation

HRID 2171605 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([C:11]2[C@@H:12]([O:20][CH3:21])[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:28])CC>C(Cl)Cl.O>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([C:11]2[C@@H:12]([O:20][CH3:21])[C@@H:13]3[C@H:18]([F:28])[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 71239417HCID 71239417, compound

Product 1

HCID 71239205HCID 71239205, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-chloro-4-((3S,3aS,4S)-4-hydroxy-3-methoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile prepared according to example 1 (30 mg, 0.0983 mmol) in DCM (2 mL) at 0° C. was added DAST (0.02 mL, 0.1475 mmol) and the reaction mixture was stirred at same temperature for 2 h. Once the starting material had disappeared (monitored by TLC), reaction mixture was diluted with DCM, water and extracted. Organic layer was washed with water, brine, dried over Na2SO4 and concentrated. Purification by preparative TLC method (40% EtOAc in hexane) provided the title compound.

Workup

  1. custom(monitored by TLC), reaction mixture
  2. extractionextracted
  3. washOrganic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by preparative TLC method (40% EtOAc in hexane)

Sources & evidence

ORD record
ord-907a2eee6afb4108b46af223ec587345
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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