(Diethylamino)sulfur trifluoride → HCID 71495924, compound

HRID 2171613Notes

Reaction equation

HRID 2171613 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][F:23])[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:30])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][F:23])[C@@H:13]3[C@H:18]([F:30])[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 89396982HCID 89396982, compound

Product 1

HCID 71495924HCID 71495924, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-chloro-4-((3S,3aS,4S)-3-(2-fluoroethoxy)-4-hydroxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile obtained in example 16 (120 mg, 0.36 mmol) in DCM (5 mL) at 0° C. was added DAST (0.05 mL, 0.43 mmol) and stirred at room temperature for 14 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 column chromatography (silica gel, 50% EtOAc in Hexane) provided the title compound (60 mg, 50%).

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 column chromatography (silica gel, 50% EtOAc in Hexane)

Sources & evidence

ORD record
ord-b39053d6b92741508b57ea3bc28127e3
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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