Sulfamide → HCID 71598626, compound

HRID 926722Notes

Reaction equation

HRID 926722 reaction equation
[S:1]([NH2:5])([NH2:4])(=[O:3])=[O:2].[F:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[C@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19]1[CH:24]=[CH:23][N:22]2[N:25]=[CH:26][C:27]([C:28]([NH:30][CH:31]3[CH2:36][CH2:35]N[CH2:33][CH2:32]3)=[O:29])=[C:21]2[CH:20]=1>O1CCOCC1>[F:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[C@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19]1[CH:24]=[CH:23][N:22]2[N:25]=[CH:26][C:27]([C:28]([NH:30][CH:31]3[CH2:36][CH2:35][N:4]([S:1](=[O:3])(=[O:2])[NH2:5])[CH2:33][CH2:32]3)=[O:29])=[C:21]2[CH:20]=1

Participants

4

Reactant 2

HCID 82267SulfamideHCID 89618564HCID 89618564, compound

Product 1

HCID 71598626HCID 71598626, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sulfamide (9 mg, 0.093 mmol) was added to solution of (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-N-(piperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide (25 mg, 0.058 mmol) (Example-32) in 1,4-Dioxane (0.5 mL) and stirring was continued at 110° C. for 4 h. The reaction mixture was concentrated to afford the residue, which was quenched with water, extracted with EtOAc, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the crude. The crude product was purified by Preparative TLC (using Silicagel GF254, 1000 u coated 20×20 cm dimension glass plate and 10% MeOH in DCM as eluent) to afford 8 mg, of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto afford the residue, which
  3. customwas quenched with water
  4. extractionextracted with EtOAc
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto afford the crude
  8. customThe crude product was purified by Preparative TLC (using Silicagel GF254, 1000 u coated 20×20 cm dimension glass plate and 10% MeOH in DCM as eluent)
  9. customto afford 8 mg

Sources & evidence

ORD record
ord-c7f173a9772042de8dcb35c7e94e079e
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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