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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
ノート
印刷プレビュー

反応式

HRID 1274395 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 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
収率 51.8%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒2 回HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bbaed464558f4d438530e040e59f2e33
出典データセット
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06156767

反応ノート

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