Dimethylformamide → 1-(3-Morpholinopropyl)-3-(3-diethylaminopropylamino)-5-chloroindazole

HRID 484887노트

반응식

HRID 484887 반응식
CN(C)C=O.[O:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][N:15]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[C:17]([NH2:25])=[N:16]2)[CH2:8][CH2:7]1.Br.Br[CH2:28][CH2:29][CH2:30][N:31]([CH2:34][CH3:35])[CH2:32][CH3:33].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O>[O:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][N:15]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[C:17]([NH:25][CH2:28][CH2:29][CH2:30][N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[N:16]2)[CH2:8][CH2:7]1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12639158(3-Bromopropyl)diethylamine hydrobromideHCID 201357631-(3-Morpholinopropyl)-3-amino-5-chloroindazole

생성물 1

HCID 201358241-(3-Morpholinopropyl)-3-(3-diethylaminopropylamino)-5-chloroindazole수율 59.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매

반응 조건

온도
80 °C

실험 절차

To 60 ml of anhydrous N,N-dimethylformamide were added 9.63 g of the 1-(3-morpholinopropyl)-3-amino-5-chloroindazole, 8.98 g of 3-bromopropyldiethylamine hydrobromide and 7.89 g of anhydrous potassium carbonate, and the mixture was stirred for 12 hours at 80° C. After cooling, the mixture was added with 80 ml of water and extracted with diethyl ether. The diethyl ether layer was extracted three times with 2N hydrochloric acid, and the hydrochloric acid layer was washed with diethyl ether. The pH of the layer was adjusted to at least 11 with potassium carbonate, and the alkali layer was extracted three times with chloroform. The chloroform layer was dried over anhydrous sodium sulfate, and chloroform was removed under reduced pressure. The residue thus obtained was subjected to an alumina-column chromatography (alumina: 200 g) using chloroform as the developing solvent to give 7.87 g of 1-(3-morpholinopropyl)-3-(3-diethylaminopropylamino)-5-chloroindazole having the following analytical values in a yield of 59 %.

후처리

  1. temperatureAfter cooling
  2. extractionextracted with diethyl ether
  3. extractionThe diethyl ether layer was extracted three times with 2N hydrochloric acid
  4. washthe hydrochloric acid layer was washed with diethyl ether
  5. extractionthe alkali layer was extracted three times with chloroform
  6. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate, and chloroform
  7. customwas removed under reduced pressure
  8. customThe residue thus obtained

출처 및 근거

ORD 기록
ord-e28df3f9611f4afab8a01517ce19ff74
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04533731

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