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

HRID 1184436ノート

反応式

HRID 1184436 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
23 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-4a34db44df8941b39db9630e869aa410
出典データセット
uspto-grants-2014_03
特許番号
US08669249B2

反応ノート

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