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Cyclohexylamine → ethyl 4-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 1969859
ノート
印刷プレビュー

反応式

HRID 1969859 の反応式
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([S:16]([C:19]3[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:14]=[CH:15][C:3]=12.[CH:26]1([NH2:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>CCCCO.O.C(Cl)Cl>[CH:26]1([NH:32][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]3[N:13]([S:16]([C:19]4[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=4)(=[O:18])=[O:17])[CH:14]=[CH:15][C:3]=23)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 7965CyclohexylamineHCID 58557443ethyl 4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

生成物 1

HCID 58558104ethyl 4-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate収率 73%

試薬・触媒・溶媒 3

HCID 2631-Butanol溶媒HCID 962Water溶媒
HCID 6344
Dichloromethane
溶媒

反応条件

温度
110 °C

実験手順

To a solution of ethyl 4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (2.28 g, 5.42 mmol) in n-BuOH (21 mL) was added cyclohexanamine (1.24 mL, 10.8 mmol). The resulting solution was heated at about 110° C. for about 18 h. The reaction mixture was cooled to ambient temperature and diluted with water and DCM (50 mL each). The layers were separated and the organic layer was dried over anhydrous Na2SO4, filtered, and concd to dryness under reduced pressure. The residue was triturated with heptane and the precipitates were filtered to give ethyl 4-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (1.74 g, 73%) as a light yellow solid: LC/MS (Table 1, Method b) Rt=3.18 min; MS m/z: 442 (M+H)+.

後処理

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customThe residue was triturated with heptane
  6. filtrationthe precipitates were filtered

出典と根拠

ORDレコード
ord-fabd4c45391349c28289b96bac153812
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08426411B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート