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

HRID 2376903노트

반응식

HRID 2376903 반응식
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]

참가 물질

7

반응물 4

HCID 8857Ethyl Acetate3회HCID 10176127Pyridinium chlorideHCID 219490931-(4-Chloropyridin-2-yl)-3-(3-diethylaminopropyl)ureaHCID 21949101N1-Methyl-5-amino-1H-1-indolecarboxamide

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 101298981-Ethoxyethanol용매

반응 조건

온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8cec70da14154797850aaf0c9e057b2b
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07468380B2

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