N-bromobutanimide → HCID 178467400, compound

HRID 928108Notes

Reaction equation

HRID 928108 reaction equation
[OH:1][C:2]([C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH2:11][CH2:10]1)([C:4]1[S:5][CH:6]=[CH:7][N:8]=1)[CH3:3].[Br:20]N1C(=O)CCC1=O>CN(C=O)C.O.C(OCC)(=O)C>[Br:20][C:6]1[S:5][C:4]([C:2]([C@H:9]2[CH2:10][CH2:11][C@H:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH2:13][CH2:14]2)([OH:1])[CH3:3])=[N:8][CH:7]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimide2×HCID 178467443HCID 178467443, compound

Product 1

HCID 178467400HCID 178467400, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-{trans-4-[1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]cyclohexyl}methanesulfonamide (178 mg, 0.59 mmol) in DMF (4.0 mL) was added N-bromosuccinimide (104 mg, 0.585 mmol) and the reaction was heated at 50° C. for one hour. The reaction was then cooled to room temperature and another portion of N-bromosuccinimide (52 mg, 0.292 mmol) was added. The reaction was then heated at 50° C. for one hour. The solution was then cooled to room temperature and diluted with water and ethyl acetate. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to afford N-{trans-4-[1-(5-bromo-1,3-thiazol-2-yl)-1-hydroxyethyl]cyclohexyl}methanesulfonamide. MS ESI calc'd. for C12H20N2O3S2 [M+H]+ 383, 385. found 383, 385. 1H NMR (500 MHz, DMSO-d6) δ 7.73 (s, 1H), 6.91 (d, J=7.4, 1H), 5.95 (s, 1H), 2.99-2.87 (m, 1H), 2.54 (s, 3H), 1.94-1.72 (m, 4H), 1.52 (t, J=11.9, 1H), 1.47-1.39 (m, 4H), 1.30-0.92 (m, 3H).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. temperatureThe reaction was then heated at 50° C. for one hour
  3. temperatureThe solution was then cooled to room temperature
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c55abe467d2545b0a30d6c3f26e63cff
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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