Ammonium Chloride → 3-[4-Chloro-3-(1-hydroxyethyl)phenyl]-1-(3,3-diphenylpropyl)-1-(2-morpholin-4-ylethyl)urea

HRID 254266

反応式

HRID 254266 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:34])[N:10]([CH2:19][CH2:20][CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:4][C:3]=1[CH:35]=[O:36].[CH3:37]Br.[Mg].[Cl-].[NH4+]>C1COCC1.C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:34])[N:10]([CH2:19][CH2:20][CH:21]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[CH:4][C:3]=1[CH:35]([OH:36])[CH3:37]

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 167371293-(4-Chloro-3-formylphenyl)-1-(3,3-diphenylpropyl)-1-(2-morpholin-4-ylethyl)ureaHCID 86584079Magnesium methylbromide

生成物 1

HCID 167371533-[4-Chloro-3-(1-hydroxyethyl)phenyl]-1-(3,3-diphenylpropyl)-1-(2-morpholin-4-ylethyl)urea収率 67%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

16 mg (0.033 mmol, 1 eq.) of 3-(4-chloro-3-formylphenyl)-1-(3,3-diphenylpropyl)-1-(2-morpholin-4-ylethyl)urea (obtained in Example 63) are dissolved in 0.7 mL of dry THF. Once the solution has been cooled to 0° C., 17 μL (0.049 mmol, 1.5 eq.) of magnesium methyl bromide in solution (3 M in diethyl ether) are added to the medium. After stirring for 20 min. at 0° C., the reaction is neutralised with a saturated ammonium chloride solution at 0° C. The aqueous phase is extracted with dichloromethane, the organic phases are washed with brine, dried over MgSO4, filtered and concentrated. The crude reaction product is subjected to chromatography over silica gel (eluent: 1/1 heptane/AcOEt). 11.4 mg of expected product are obtained (yield=67%).

後処理

  1. extractionThe aqueous phase is extracted with dichloromethane
  2. washthe organic phases are washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude reaction product

出典と根拠

ORDレコード
ord-aeffb95afd854c909d4eb47d8fd5da6d
出典データセット
uspto-grants-2011_01
特許番号
US07875609B2

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