Methanesulfonyl chloride → HCID 86611181, compound

HRID 2384159Notes

Reaction equation

HRID 2384159 reaction equation
[CH:1]1([N:7]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[C:14]([CH:16]=[N:17][OH:18])[N:15]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:25][S:26](Cl)(=[O:28])=[O:27].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:19]1([N:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[C:14]([C:16]([S:26]([CH3:25])(=[O:28])=[O:27])=[N:17][OH:18])[N:15]=2)=[O:9])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86611182HCID 86611182, compound

Product 1

HCID 86611181HCID 86611181, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dicyclohexyl-3-[4-(hydroxyimino-methyl)-thiazol-2-yl]-urea (0.15 mmol) in DCM (4 mL) was added methansulfonyl chloride (0.15 mmol) and DIEA (0.15 mL). The mixture was stirred at rt for 2 h and quenched with water (10 mL). The reaction mixture was extracted with ethyl acetate (3×10 mL). The combined organic extracts was washed with water (2×30 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (silica, EtOAc/hexanes 1:4 to EtOAc/hexanes 1:1) to give the desired product in 30% yield.

Workup

  1. customquenched with water (10 mL)
  2. extractionThe reaction mixture was extracted with ethyl acetate (3×10 mL)
  3. washThe combined organic extracts was washed with water (2×30 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (silica, EtOAc/hexanes 1:4 to EtOAc/hexanes 1:1)

Sources & evidence

ORD record
ord-af4950dbd0d24f7dbfc78b6107bab4e8
Source dataset
uspto-grants-2012_09
Patent number
US08263634B2

Reaction notes

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