Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 25069654、化合物

HRID 876688ノート

反応式

HRID 876688 の反応式
CO[C:3](=[O:18])[C:4]([C:9]1[S:10][C:11]([C:14]([F:17])([F:16])[F:15])=[N:12][N:13]=1)=[CH:5][N:6](C)C.[NH:19]([C:21]1[CH:26]=[C:25]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[N:24]=[CH:23][N:22]=1)N.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.CC[O-].[Na+].C[O-].[Na+]>C(O)C.CO>[N:27]1([C:25]2[N:24]=[CH:23][N:22]=[C:21]([N:19]3[C:3](=[O:18])[C:4]([C:9]4[S:10][C:11]([C:14]([F:15])([F:16])[F:17])=[N:12][N:13]=4)=[CH:5][NH:6]3)[CH:26]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

参加物

8

反応物 5

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 2723922Sodium ethoxideHCID 10942334Sodium MethoxideHCID 441403054-Hydrazinyl-6-(piperidin-1-yl)pyrimidineHCID 674565093-(Dimethylamino)-2-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]acrylic acid methyl ester

生成物 1

HCID 25069654HCID 25069654、化合物

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 887Methanol溶媒

実験手順

240 mg (854 μmol) of the compound from Example 2A, 150 mg (776 mmol) of the compound from Example 8A and 18 mg (78 mmol) camphor-10-sulfonic acid are dissolved in 3 ml anhydrous ethanol and the mixture is heated under reflux overnight. After cooling, 64 mg (931 mmol) sodium ethylate are added and the mixture is further stirred overnight at RT. The precipitate formed is filtered off with suction, washed with ethanol and diethyl ether and dried. The filtrate is concentrated and the residue is purified by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient). The two intermediate product fractions obtained in this way are suspended together in 5 ml methanol, 15 mg (278 μmol) sodium methylate are added and the mixture is heated under reflux overnight. After cooling, the reaction mixture is purified by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient) and 26 mg (8% of th.) of the title compound are obtained.

後処理

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. customThe precipitate formed
  5. filtrationis filtered off with suction
  6. washwashed with ethanol and diethyl ether
  7. customdried
  8. concentrationThe filtrate is concentrated
  9. customthe residue is purified by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)
  10. customThe two intermediate product fractions obtained in this way
  11. temperaturethe mixture is heated
  12. temperatureunder reflux overnight
  13. temperatureAfter cooling
  14. customthe reaction mixture is purified by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient) and 26 mg (8% of th.) of the title compound
  15. customare obtained

出典と根拠

ORDレコード
ord-767e5735fb52400892e9234aa418626e
出典データセット
uspto-grants-2015_03
特許番号
US08987261B2

反応ノート

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