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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Sulfuric acid magnesium salt (1:1) → 1-(7-Aza-bicyclo[2.2.1]hept-7-yl)-2-{2-(3,5-dimethylphenyl)-3-[2-(2-pyridin-3-yl-ethylamino)-ethyl]-1H-indol-5-yl)-2-methylpropan-1-one

HRID 1274395
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HRID 1274395 반응식
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([CH3:24])([CH3:23])[C:14]([N:16]3[CH:20]4[CH2:21][CH2:22][CH:17]3[CH2:18][CH2:19]4)=[O:15])[CH:11]=2)[NH:6][C:5]=1[C:25]1[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[CH:26]=1.S([O-])([O-])(=O)=O.[Mg+2].[N:39]1[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][CH:46]=O)[CH:40]=1.C([BH3-])#N.[Na+]>C(Cl)(Cl)Cl.CO.C(O)(=O)C>[CH:17]12[N:16]([C:14](=[O:15])[C:13]([C:10]3[CH:11]=[C:12]4[C:7](=[CH:8][CH:9]=3)[NH:6][C:5]([C:25]3[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[CH:26]=3)=[C:4]4[CH2:3][CH2:2][NH:1][CH2:46][CH2:45][C:41]3[CH:40]=[N:39][CH:44]=[CH:43][CH:42]=3)([CH3:24])[CH3:23])[CH:20]([CH2:19][CH2:18]1)[CH2:21][CH2:22]2
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참가 물질

8

반응물 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 5003444Sodium cyanoborohydrideHCID 11073404Pyridin-3-ylacetaldehydeHCID 117617912-[3-(2-Aminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-(7-azabicyclo[2.2.1]hept-7-yl)-2-methyl-propan-1-one

생성물 1

HCID 221206711-(7-Aza-bicyclo[2.2.1]hept-7-yl)-2-{2-(3,5-dimethylphenyl)-3-[2-(2-pyridin-3-yl-ethylamino)-ethyl]-1H-indol-5-yl)-2-methylpropan-1-one
수율 51.8%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매2회HCID 6212Chloroform용매

실험 절차

To a solution of 2-[3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-(7-aza-bicyclo[2.2.1]hept-7-yl)-2-methylpropan-1-one (183 mg in 10 mL dry chloroform) at 0° C. was added 305 mg magnesium sulfate followed by a solution of 100 mg pyridin-3-yl-acetaldehyde in 1.0 mL chloroform and the mixture stirred at low temperature. After 6 minutes, a solution of 52 mg sodium cyanoborohydride in 0.80 mL methanol was added and the pH djusted to pH6 by the addition of 10% acetic acid in methanol. After 30 minutes, the reaction was quenched by the addition of saturated sodium bicarbonate and the mixture extracted with ethyl acetate. The organic portion was washed successively with saturated ammonium chloride, sodium bicarbonate and brine, then dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol, 93:7; then 88:12) gave the title compound (118 mg).

후처리

  1. waitAfter 30 minutes
  2. customthe reaction was quenched by the addition of saturated sodium bicarbonate
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe organic portion was washed successively with saturated ammonium chloride, sodium bicarbonate and brine
  5. dry with materialdried over sodium sulfate
  6. customPurification of the
  7. concentrationconcentrate by flash chromatography on silica gel (methylene chloride

출처 및 근거

ORD 기록
ord-bbaed464558f4d438530e040e59f2e33
출처 데이터셋
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06156767

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