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Sodium Bicarbonate → Methyl 4-(4-{[(3-cyano-4-phenyl-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)sulfanyl]methyl}-1,3-thiazol-2-yl)benzoate

HRID 1916274
ノート
印刷プレビュー

反応式

HRID 1916274 の反応式
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)[S:6][CH:7]=1.C(=O)(O)[O-].[Na+].[C:23]([C:25]1[C:26]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:27]2[CH2:34][CH2:33][CH2:32][C:28]2=[N:29][C:30]=1[S-:31])#[N:24].[Na+]>O>[C:23]([C:25]1[C:26]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:27]2[CH2:34][CH2:33][CH2:32][C:28]2=[N:29][C:30]=1[S:31][CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)[S:6][CH:7]=1)#[N:24]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 45156786Methyl 4-[4-(chloromethyl)-1,3-thiazol-2-yl]benzoateHCID 66932949Sodium [3-cyano-4-phenyl-6,7-dihydro-5H-cyclopenta[b]pyridine-2-thiolate]

生成物 1

HCID 44133054Methyl 4-(4-{[(3-cyano-4-phenyl-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)sulfanyl]methyl}-1,3-thiazol-2-yl)benzoate

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

実験手順

315 mg (1.18 mmol) of methyl 4-[4-(chloromethyl)-1,3-thiazol-2-yl]benzoate (prepared as described in WO 2005/011685) and 329 mg (3.92 mmol) of sodium bicarbonate are added to the reaction mixture from Example 18A, and the mixture is stirred at RT for 16 h. 50 ml of water were added, and the reaction was extracted with ethyl acetate. The organic phase was washed with water and a saturated aqueous sodium chloride solution, dried over magnesium sulfate and freed from the solvent on a rotary evaporator. The residue was purified by preparative HPLC (column: YMC GEL ODS-AQ S-5, 15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

後処理

  1. extractionthe reaction was extracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, dried over magnesium sulfate
  4. customfreed from the solvent on a rotary evaporator
  5. customThe residue was purified by preparative HPLC (column: YMC GEL ODS-AQ S-5, 15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

出典と根拠

ORDレコード
ord-015d5404084443ecad8826b73ed9bda9
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08618119B2

反応ノート

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