Sulfamide → HCID 71598626, compound

HRID 2167785Notes

Reaction equation

HRID 2167785 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-a816cf76a76b494d931ca1d5ba212366
Source dataset
uspto-grants-2015_06
Patent number
US09045479B2

Reaction notes

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