Diisopropylethylamine → 4-Bromophenyl 4-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

HRID 1518447

反応式

HRID 1518447 の反応式
Cl.[CH3:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[CH:14][C:13]2=[O:25])=[CH:8][CH:7]=1)(=[O:5])=[O:4].C(N(C(C)C)CC)(C)C.Cl[C:36]([O:38][C:39]1[CH:44]=[CH:43][C:42]([Br:45])=[CH:41][CH:40]=1)=[O:37]>C(Cl)Cl>[CH3:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]3[CH2:24][CH2:23][N:22]([C:36]([O:38][C:39]4[CH:44]=[CH:43][C:42]([Br:45])=[CH:41][CH:40]=4)=[O:37])[CH2:21][CH2:20]3)=[CH:14][C:13]2=[O:25])=[CH:8][CH:7]=1)(=[O:4])=[O:5]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 52377364-Bromophenyl chloroformateHCID 673669641-(4-(methylsulfonyl)phenyl)-4-(piperidin-4-yloxy)pyridin-2(1H)-one hydrochloric acid

生成物 1

HCID 673694054-Bromophenyl 4-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate収率 73%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

To a mixture of 1-(4-(methylsulfonyl)phenyl)-4-(piperidin-4-yloxy)pyridin-2(1H)-one hydrochloric acid (154 mg, 0.40 mmol) and diisopropylethylamine (0.35 mL, 0.20 mmol) in CH2Cl2 (1.5 mL) at room temperature was added 4-bromophenyl chloroformate (prepared according to procedures described at Step B of Example 2 substituting 4-bromophenol for 1,1,1-trifluoro-2-propanol) in CH2Cl2 (1.0 mL). The resulting mixture was stirred at room temperature for 3 hrs, diluted with CH2Cl2 and washed with water and brine. The organic layer was dried (Na2SO4) and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel (0-100% EtOAc/Hexanes) to give the title compound (159 mg, 73%) as a light yellow solid. MS (ESI) 547, 549 (M+H).

後処理

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated under reduced pressure
  4. customThe crude product was purified by flash chromatography on silica gel (0-100% EtOAc/Hexanes)

出典と根拠

ORDレコード
ord-a032ffce11104895bd5fc92c4a7bc1cc
出典データセット
uspto-grants-2012_07
特許番号
US08232404B2

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