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

HRID 1676177노트

반응식

HRID 1676177 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e15d6a5620484623864d2415dab326ad
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003796B2

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