HCID 71239513, compound → HCID 71241199, compound

HRID 2171614Notes

Reaction equation

HRID 2171614 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[CH2:18][C@@H:17]([OH:19])[CH2:16][N:14]3[N:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]>C(Cl)Cl.C(OCC)(=O)C.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[CH2:18][C:17](=[O:19])[CH2:16][N:14]3[N:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 1

HCID 71239513HCID 71239513, compound

Product 1

HCID 71241199HCID 71241199, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-4-((3S,3aS,5R)-5-hydroxy-3-(2-methoxyethoxy)-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile (50 mg, 0.143 mmol) in DCM (5 mL) at 0° C. was added Dessmartin reagent (121 mg, 0.286 mmol) and reaction mixture was stirred at room temperature for 16 h. Once the starting material had disappeared (monitored by TLC), reaction mixture was diluted with ethyl acetate, water and extracted. Organic layer was washed with saturated NaHCO3 solution, water, and brine then dried over Na2SO4 and concentrated. Purification by column chromatography (silica gel, 1% MeOH in DCM) provided the title compound (36 mg, 73%).

Workup

  1. custom(monitored by TLC), reaction mixture
  2. extractionextracted
  3. washOrganic layer was washed with saturated NaHCO3 solution, water, and brine
  4. dry with materialthen dried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by column chromatography (silica gel, 1% MeOH in DCM)

Sources & evidence

ORD record
ord-a5af018dc65345a2b7f1039365f934a3
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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