Sodium Iodide → N-[1-[3-(2-methoxycarbonylphenoxy)propan-1-yl]piperidin-4-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide

HRID 1978525ノート

反応式

HRID 1978525 の反応式
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]([C:12]2[S:22][C:21]3[N:23]4[C:14](=[CH:15][N:16]=[C:17]4[CH:18]=[CH:19][CH:20]=3)[CH:13]=2)=[O:11])[CH2:5][CH2:4]1.C(N(CC)CC)C.C1CCN2C(=NCCC2)CC1.[I-].[Na+].Cl[CH2:45][CH2:46][CH2:47][O:48][C:49]1[CH:58]=[CH:57][CH:56]=[CH:55][C:50]=1[C:51]([O:53][CH3:54])=[O:52]>C(#N)C>[CH3:54][O:53][C:51]([C:50]1[CH:55]=[CH:56][CH:57]=[CH:58][C:49]=1[O:48][CH2:47][CH2:46][CH2:45][N:3]1[CH2:4][CH2:5][CH:6]([NH:9][C:10]([C:12]2[S:22][C:21]3[N:23]4[C:14](=[CH:15][N:16]=[C:17]4[CH:18]=[CH:19][CH:20]=3)[CH:13]=2)=[O:11])[CH2:7][CH2:8]1)=[O:52]

参加物

7

反応物 5

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15285144Methyl 2-(3-chloro-1-propoxy)benzoateHCID 21994154N-(piperidin-4-yl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride

生成物 1

HCID 21993853N-[1-[3-(2-methoxycarbonylphenoxy)propan-1-yl]piperidin-4-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide収率 77%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 0.80 g (2.14 mmol.) of N-(piperidin-4-yl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride, 1.5 ml (10.76 mmol.) of triethylamine and 0.65 g (4.27 mmol.) of 1,8-diazabicyclo[5.4.0]unde-7-cene (DBU) in acetonitrile (20 ml) were added, at room temperature, 0.38 g of sodium iodide and 0.59 g (2.58 mmol.) of methyl 2-(3-chloro-1-propoxy)benzoate. The mixture was heated under reflux for 3 days under nitrogen atmosphere. The solvent was distilled off under reduced pressure. To the residue was added water, which was subjected to extraction with chloroform. The organic layer was washed with a saturated aqueous saline solution, which was dried over magnesium sulfate, followed by concentration. The concentrate was purified by means of a column chromatography (methanol/ethyl acetate 30-50%), followed by distilling off the solvent under reduced pressure to afford the object compound (0.81 g, 77%) as a reddish amorphous product.

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 days under nitrogen atmosphere
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionTo the residue was added water, which
  5. extractionwas subjected to extraction with chloroform
  6. washThe organic layer was washed with a saturated aqueous saline solution, which
  7. dry with materialwas dried over magnesium sulfate
  8. concentrationfollowed by concentration
  9. customThe concentrate was purified by means of a column chromatography (methanol/ethyl acetate 30-50%)
  10. distillationby distilling off the solvent under reduced pressure

出典と根拠

ORDレコード
ord-02076747396241aa8b92daa15472f96a
出典データセット
uspto-grants-2001_05
特許番号
US06235731B1

反応ノート

読み込み中…