Ethyl Acetate → 5-(2-(3-(3-Diethylaminopropyl)ureido)pyridin-4-ylamino)indole-1-carboxylic acid methylamide

HRID 2376903ノート

反応式

HRID 2376903 の反応式
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[O:10])[CH:3]=1.Cl.N1C=CC=CC=1.[CH3:27][NH:28][C:29]([N:31]1[C:39]2[C:34](=[CH:35][C:36]([NH2:40])=[CH:37][CH:38]=2)[CH:33]=[CH:32]1)=[O:30].C(OCC)(=O)C>C(OC(O)C)C.CO>[CH3:27][NH:28][C:29]([N:31]1[C:39]2[C:34](=[CH:35][C:36]([NH:40][C:2]3[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[O:10])[CH:3]=3)=[CH:37][CH:38]=2)[CH:33]=[CH:32]1)=[O:30]

参加物

7

反応物 4

HCID 8857Ethyl Acetate3 回HCID 10176127Pyridinium chlorideHCID 219490931-(4-Chloropyridin-2-yl)-3-(3-diethylaminopropyl)ureaHCID 21949101N1-Methyl-5-amino-1H-1-indolecarboxamide

生成物 1

HCID 210548055-(2-(3-(3-Diethylaminopropyl)ureido)pyridin-4-ylamino)indole-1-carboxylic acid methylamide収率 17%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 101298981-Ethoxyethanol溶媒

反応条件

温度
130 °C

実験手順

1-(4-Chloropyridin-2-yl)-3-(3-diethylaminopropyl)urea (30 mg, 0.11 mmol) was dissolved in ethoxyethanol (1.1 ml); pyridine hydrochloride (24 mg, 0.22 mmol) and 5-aminoindole-1-carboxylic acid methylamide (22 mg, 0.12 mmol, Production example 218-2) was added thereto; and the reaction mixture was stirred at 130° C. for 2 hours. After cooled down to room temperature, the reaction mixture was partitioned between a saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate; and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia NH, hexane:ethyl acetate=1:3, ethyl acetate, ethyl acetate:methanol=93:7 in this order) to yield the title compound (8 mg, 0.018 mmol, 17%) as pale yellow powder.

後処理

  1. temperatureAfter cooled down to room temperature
  2. customthe reaction mixture was partitioned between a saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate
  3. washand the organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Fuji Silysia NH, hexane

出典と根拠

ORDレコード
ord-8cec70da14154797850aaf0c9e057b2b
出典データセット
uspto-grants-2008_12
特許番号
US07468380B2

反応ノート

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