Triethylamine → 2-(4-tert-Butylphenoxy)-N-{4-[(ethylsulfonyl)amino]benzyl}acetamide

HRID 1350849

反応式

HRID 1350849 の反応式
[C:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([OH:13])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])=[CH:21][CH:20]=1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]([NH:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([NH:25][S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])=[CH:23][CH:24]=2)=[O:13])=[CH:14][CH:15]=1)([CH3:2])([CH3:3])[CH3:4]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 157182-(4-Tert-butylphenoxy)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21097533N-[4-(aminomethyl)phenyl]ethane-1-sulfonamide hydrochloride

生成物 1

HCID 586404232-(4-tert-Butylphenoxy)-N-{4-[(ethylsulfonyl)amino]benzyl}acetamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To a N,N-dimethylformamide (DMF) (5 ml) solution of (4-tert-butylphenoxy)acetic acid (330 mg, 1.50 mmol) and N-[4-(aminomethyl)phenyl]ethanesulfonamide hydrochloride (451 mg, 1.80 mmol, Journal of Medicinal Chemistry 2003, 46(14), 3116–3126), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (431 mg, 2.25 mmol), 4-(dimethylamino)pyridine (DMAP) (46 mg, 0.38 mmol) and triethylamine (506 mg, 5.0 mmol) were added and the mixture was stirred for 15 hours at ambient temperature. The reaction mixture was then quenched with saturated aqueous solution of sodium bicarbonate and then crude products were extracted with methylene dichloride The organic layer was then washed with brine, dried over sodium sulfate. After filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give a residue, which was applied to an amino bound silica gel chromatography column and eluted with methylene dichloride/methanol=100/1 to furnish the title compound. Further, the title compound was recrystallized from ethyl acetate and hexane to furnish 341 mg (56% yield) of the title compound as a white solid.

後処理

  1. customThe reaction mixture was then quenched with saturated aqueous solution of sodium bicarbonate
  2. extractioncrude products were extracted with methylene dichloride The organic layer
  3. washwas then washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. customto separate solvent and sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customto give a residue, which
  9. washeluted with methylene dichloride/methanol=100/1

出典と根拠

ORDレコード
ord-d1d222ab2acd40b7a3c8d9ec1738f8f6
出典データセット
uspto-grants-2007_05
特許番号
US07214824B2

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