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Hydrochloric Acid → N-(1H-indol-1-yl)-N-propyl-9H-purin-6-amine

HRID 465968
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HRID 465968 반응식
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.Cl.[N:12]1([NH:21][CH2:22][CH2:23][CH3:24])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1.C([O-])([O-])=O.[Na+].[Na+]>CN1CCCC1=O.O>[N:12]1([N:21]([CH2:22][CH2:23][CH3:24])[C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][NH:6]3)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 53592776-ChloropurineHCID 107023901H-Indol-1-amine, N-propyl-

생성물 1

HCID 178456864N-(1H-indol-1-yl)-N-propyl-9H-purin-6-amine수율 25.1%

시약·촉매·용매 2

HCID 962Water용매
HCID 13387
N-methyl-2-pyrrolidone
용매
2회

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온도
120 °C

실험 절차

To a solution of 6-chloropurine (5.0 g, 0.032 mole) in 50 ml 1-methyl-2-pyrrolidinone, was added 1 ml ethereal-HCl; followed by a solution of N-(1H-indol-1-yl)-N-propylamine (5.2 g, 0.030 mole) in 50 ml 1-methyl-2-pyrrolidinone. After stirring at 120° C. for six hours, the mixture was cooled, poured into 500 ml water and stirred for five minutes, pH adjusted to 10 with Na2CO3 ; then extracted with ethyl acetate. The organic layer was washed with water, then dried (saturated NaCl, anhydrous MgSO4). After filtering, the solution was evaporated to an oil, about 8 g, which was eluted on a silica gel column with ethyl acetate via high pressure liquid chromatography. The desired fractions were combined, then evaporated to yield 2.2 g (25%) of N-(1H-indol-1-yl)-N-propyl-9H-purin-6-amine, m.p. 90°-5° C.

후처리

  1. temperaturethe mixture was cooled
  2. stirringstirred for five minutes
  3. extractionthen extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  6. filtrationAfter filtering
  7. customthe solution was evaporated to an oil, about 8 g, which
  8. washwas eluted on a silica gel column with ethyl acetate via high pressure liquid chromatography
  9. customevaporated

출처 및 근거

ORD 기록
ord-5e21a73129ce470a9cdb6208078de0f6
출처 데이터셋
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05155098

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