Methanesulfonyl chloride → 1-{4-Chloro-6-[(ethylamino)carbonyl]-3',5'-difluoro-5-methylbiphenyl-2-yl}ethyl methanesulfonate

HRID 1499726Notes

Reaction equation

HRID 1499726 reaction equation
[Cl:1][C:2]1[C:3]([CH3:24])=[C:4]([C:19]([NH:21][CH2:22][CH3:23])=[O:20])[C:5]([C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=2)=[C:6]([CH:8]([OH:10])[CH3:9])[CH:7]=1.C(N(CC)C(C)C)(C)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[CH3:34][S:35]([O:10][CH:8]([C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([CH3:24])=[C:4]([C:19]([NH:21][CH2:22][CH3:23])=[O:20])[C:5]=1[C:11]1[CH:12]=[C:13]([F:18])[CH:14]=[C:15]([F:17])[CH:16]=1)[CH3:9])(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 866776614-Chloro-N-ethyl-3',5'-difluoro-6-(1-hydroxyethyl)-3-methylbiphenyl-2-carboxamide

Product 1

HCID 866776621-{4-Chloro-6-[(ethylamino)carbonyl]-3',5'-difluoro-5-methylbiphenyl-2-yl}ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-chloro-N-ethyl-3′,5′-difluoro-6-(1-hydroxyethyl)-3-methylbiphenyl-2-carboxamide (185 mg, 0.523 mmol) in methylene chloride (3 mL) was added N,N-diisopropylethylamine (0.18 mL, 1.0 mmol), followed by methanesulfonyl chloride (0.061 mL, 0.78 mmol). The reaction was stirred at rt for 10 min, quenched by pouring onto iced water, and extracted with dichloromethane. The combined organic layers were washed with aq. sodium bicarbonate, dried over magnesium sulfate, and evaporated to dry. The residue was used directly in next step (0.226 g, 100%). LCMS calculated for C19H21ClF2NO4S (M+H)+: m/z=432.1; Found: 432.1.

Workup

  1. customquenched
  2. additionby pouring onto iced water
  3. extractionextracted with dichloromethane
  4. washThe combined organic layers were washed with aq. sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto dry

Sources & evidence

ORD record
ord-8edd8f61f7144d5a849ede6bea9db7e4
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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