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2-Mercaptoethanol → 6-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-2-[(2-hydroxyethyl)thio]pyrimidine-4-carboxylic acid

HRID 2233914
ノート
印刷プレビュー

反応式

HRID 2233914 の反応式
Cl[C:2]1[NH:7][C:6]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19]([C:21]3[NH:22][C:23]([CH3:28])=[C:24]([Cl:27])[C:25]=3[Cl:26])=[O:20])[CH2:14][CH2:13]2)(C(OC)=O)[CH:5]=[CH:4][N:3]=1.[SH:29][CH2:30][CH2:31][OH:32].[C:33](=O)([O-:35])[O-:34].[K+].[K+]>CN(C=O)C.CCOC(C)=O.Cl>[Cl:26][C:25]1[C:24]([Cl:27])=[C:23]([CH3:28])[NH:22][C:21]=1[C:19]([NH:18][CH:15]1[CH2:14][CH2:13][N:12]([C:6]2[N:7]=[C:2]([S:29][CH2:30][CH2:31][OH:32])[N:3]=[C:4]([C:33]([OH:35])=[O:34])[CH:5]=2)[CH2:17][CH2:16]1)=[O:20]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 15672-MercaptoethanolHCID 11430Potassium CarbonateHCID 178499026HCID 178499026、化合物

生成物 1

HCID 685800786-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-2-[(2-hydroxyethyl)thio]pyrimidine-4-carboxylic acid収率 24.2%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒
HCID 6228
Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

A suspension of methyl 2-chloro-6-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)pyrimidine-4-carboxylate (Example 6, 150 mg, 0.34 mmol), 2-mercaptoethanol (31 mg, 0.40 mmol) and potassium carbonate (139 mg, 1.01 mmol) in DMF (3 ml) were stirred at 65° C. under nitrogen for 3 hours. The mixture was cooled to room temperature and diluted with EtOAc (75 ml) and 1 N HCl (3 ml). The organic layer was separated, dried over Na2SO4, filtered and concentrated under vacuum. Purification of the residue by reversed-phase HPLC (water/acetonitrile gradient, 10-95%) gave 39 mg of the title compound.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customPurification of the residue by reversed-phase HPLC (water/acetonitrile gradient, 10-95%)

出典と根拠

ORDレコード
ord-01a44b4e4353461cbf9c0471942bb24d
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07709503B2

反応ノート

読み込み中…

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