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

HRID 1499726ノート

反応式

HRID 1499726 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8edd8f61f7144d5a849ede6bea9db7e4
出典データセット
uspto-grants-2015_12
特許番号
US09199982B2

反応ノート

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