Sulfamide → HCID 66666614, compound

HRID 1618029Notes

Reaction equation

HRID 1618029 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:21][CH:20]=2)[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[O:11])=[C:4]([CH3:31])[CH:3]=1.[S:32](N)([NH2:35])(=[O:34])=[O:33]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:19]2[CH:20]=[CH:21][C:22]([CH:25]3[CH2:26][CH2:27][N:28]([S:32]([NH2:35])(=[O:34])=[O:33])[CH2:29][CH2:30]3)=[CH:23][CH:24]=2)[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[O:11])=[C:4]([CH3:31])[CH:3]=1

Participants

4

Reactant 2

HCID 82267SulfamideHCID 66666314HCID 66666314, compound

Product 1

HCID 66666614HCID 66666614, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (R)-3-(4-chloro-2-methylphenyl)-1-(2-methylpyridin-4-yl)-3-(4-(piperidin-4-yl)phenyl)propan-1-one (60 mg, 0.14 mmol) and sulfamide (20 mg, 0.21 mmol) in 1,4-dioxane (5 mL) was stirred for 17 h at 108° C., then partitioned between sat. aq. ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated. Flash chromatography (silica gel, 50% to 100% EtOAc in heptane) afforded the title compound (59 mg, 83%). White foam, MS (ESI+): m/z=512.3 ([M+H]+).

Workup

  1. custompartitioned between sat. aq. ammonium chloride solution and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3ee1140a31b843aca8559c047cb3d2f5
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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