Triethylamine → 2-[4-tert-Butyl-3-(2-methoxyethoxy)phenoxy]-N-{3-fluoro-4-[(methylsulfonyl)amino]benzyl}acetamide

HRID 1350865Notes

Reaction equation

HRID 1350865 reaction equation
[C:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([OH:13])=O)=[CH:7][C:6]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])=[C:38]([F:47])[CH:37]=1.C(N(CC)CC)C>O1CCCC1>[C:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([NH:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])=[C:38]([F:47])[CH:37]=2)=[O:13])=[CH:7][C:6]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 21097495[4-Tert-butyl-3-(2-methoxyethoxy)phenoxy]acetic acidHCID 21097525N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochloride

Product 1

HCID 210974552-[4-tert-Butyl-3-(2-methoxyethoxy)phenoxy]-N-{3-fluoro-4-[(methylsulfonyl)amino]benzyl}acetamideYield 46.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (THF) (3 ml) solution of [4-tert-butyl-3-(2-methoxyethoxy)phenoxy]acetic acid (100 mg, 0.35 mmol) was added 1,1′-carbonyl-diimidazole (63 mg, 0.39 mmol) and the mixture was stirred for 1 hour at ambient temperature. To the mixture was added N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochloride (99 mg, 0.39 mmol) and triethyl amine (150 ul, 1.1 mmol) and the mixture was stirred for 1 hour at ambient temperature. After filtration to separate solvent and the resulting percipitate, the solvent was removed under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with ethyl acetate/hexane=1/1 to furnish 78 mg (46% yield) of the title compound as a white solid.

Workup

  1. stirringthe mixture was stirred for 1 hour at ambient temperature
  2. filtrationAfter filtration
  3. customto separate solvent
  4. customthe resulting percipitate, the solvent was removed under reduced pressure
  5. customto give a residue, which
  6. washeluted with ethyl acetate/hexane=1/1

Sources & evidence

ORD record
ord-a0d8bbd53f5b40ca9055b411eb840fe3
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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