Ammonium Chloride → Methyl 3-(3'-{3-[2-(4-fluorophenyl)ethyl]-1-methylureido}biphenyl-4-yl)propanoate

HRID 250828Notes

Reaction equation

HRID 250828 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][CH2:7][N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[CH3:13][NH:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1.[Cl-].[NH4+]>O1CCCC1.C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:10])[N:14]([C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:23][CH:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH3:13])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 52048021-Fluoro-4-(2-isocyanatoethyl)benzeneHCID 67273433Methyl 3-(3'-methylaminobiphenyl-4-yl)propanoate

Product 1

HCID 67272001Methyl 3-(3'-{3-[2-(4-fluorophenyl)ethyl]-1-methylureido}biphenyl-4-yl)propanoateYield 55.3%

Reagents, catalysts & solvents 1

HCID 68616177Triethylamine tetrahydrofuranSolvent

Procedure

340 μL (1.84 mmol, 2 eq) of 4-fluorophenethyl isocyanate are added to a solution of 250 mg (0.92 mmol, 1 eq) of methyl 3-(3′-methylaminobiphenyl-4-yl)propanoate in 8 mL of a 4/1 tetrahydrofuran/triethylamine mixture. The reaction mixture is stirred for 24 hours at room temperature. The reaction is stopped by addition of 10 mL of saturated ammonium chloride solution and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate). 221 mg of methyl 3-(3′-{3-[2-(4-fluorophenyl)ethyl]-1-methylureido}biphenyl-4-yl)propanoate are obtained. Yield=55%

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-673739c7a05c433aa8f596d0b0abe4b1
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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