Piperidine → 6-(1-Piperidinylsulfonyl)-2H-1,4-benzoxazin-3(4H)-one

HRID 1184436노트

반응식

HRID 1184436 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-])=O.[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)CC)C.Br[CH2:29][C:30](OC)=[O:31]>C(Cl)Cl>[N:15]1([S:8]([C:5]2[CH:6]=[CH:7][C:2]3[O:1][CH2:29][C:30](=[O:31])[NH:12][C:3]=3[CH:4]=2)(=[O:10])=[O:9])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

참가 물질

6

반응물 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 36704794-Hydroxy-3-nitrobenzene-1-sulfonyl chloride

생성물 1

HCID 41720586-(1-Piperidinylsulfonyl)-2H-1,4-benzoxazin-3(4H)-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
23 °C

실험 절차

To a 15 mL screw cap vial was added 4-hydroxy-3-nitrobenzene-1-sulfonyl chloride (238 mg, 1.0 mmol) and piperidine (102 mg, 1.2 mmol) in DCM (5.0 mL) followed by triethylamine (346 μL, 2.5 mmol). After stirring at 23° C. for 1 h, the reaction was concentrated in vacuo and the resulting residue was taken up in sat aqueous NaHCO3. The resulting solid was isolated by filtration, washed with water and dried in vacuo to give a white solid. The material was subsequently alkylated using the general procedure for alkylation of substituted 2-nitrophenols using methyl bromoacetate as the alkylating agent followed by treatment in the general procedure for reduction of nitro group and subsequent ring closure to give the title compound as a white solid: 1H NMR (DMSO-d6, 400 MHz): δ=10.91 (s, 1H), 7.21-7.32 (m, 2H), 7.15 (d, J=8.1 Hz, 1H), 4.71 (s, 2H), 2.85 (t, J=5.1 Hz, 4H), 1.46-1.62 (m, 4H), 1.37 ppm (d, J=5.1 Hz, 2H). ESI-MS: m/z 297.1 (M+H)+.

후처리

  1. customTo a 15 mL screw cap
  2. concentrationthe reaction was concentrated in vacuo
  3. customThe resulting solid was isolated by filtration
  4. washwashed with water
  5. customdried in vacuo
  6. customto give a white solid

출처 및 근거

ORD 기록
ord-4a34db44df8941b39db9630e869aa410
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669249B2

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