Methanol → HCID 86729634、化合物

HRID 2284906ノート

反応式

HRID 2284906 の反応式
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[C:5]([Cl:18])=[CH:4][N:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH2:27]2)=[CH:22][C:21]=1[O:35][CH3:36].CO>C(Cl)(Cl)Cl>[Cl:18][C:5]1[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])=[N:7][C:2]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH2:27]3)=[CH:22][C:21]=2[O:35][CH3:36])=[N:3][CH:4]=1

参加物

5

反応物 3

HCID 887MethanolHCID 552327374-(4-Acetyl-1-piperazinyl)-2-(methyloxy)anilineHCID 59362999HCID 59362999、化合物

生成物 1

HCID 86729634HCID 86729634、化合物

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of 2,5-dichloro-4-(2-nitrophenoxy)pyrimidine (300 mg, 1.052 mmol) in 0.08M p-PTSA/1,4-dioxane (10 mL) was added 1-(4-(4-amino-3-methoxy phenyl)piperazin-1-yl)ethanone (262 mg, 1.052 mmol), and the mixture was heated to 100° C. for 16 h. TLC showed completion of starting material (TLC system: 5% methanol in chloroform (Rf): 0.4). 1,4-dioxane was evaporated under reduced pressure, and the remainder was diluted with ethyl acetate (35 mL) and the remainder was washed with water (10 mL) followed by saturated NaHCO3 solution (10 mL). The organic layer was separated, dried over sodium sulphate, and concentrated. Crude compound was purified by column chromatography using silica gel (100-200 mesh) with 3% methanol in chloroform to obtain 1-(4-(4-(5-chloro-4-(2-nitrophenoxy)pyrimidin-2-ylamino)-3-methoxyphenyl) piperazin-1-yl)ethanone as a grey solid. (Yield: 140 mg, 26.6%). MS: m/z 308.4 (ES+, M+H).

後処理

  1. custom1,4-dioxane was evaporated under reduced pressure
  2. additionthe remainder was diluted with ethyl acetate (35 mL)
  3. washthe remainder was washed with water (10 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customCrude compound was purified by column chromatography

出典と根拠

ORDレコード
ord-66f949743e3445238808b142d0d12721
出典データセット
uspto-grants-2015_09
特許番号
US09145387B2

反応ノート

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