1,2-Dichloroethane → HCID 69332958, compound

HRID 354278Notes

Reaction equation

HRID 354278 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([OH:23])=O)[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11].[CH2:24]([O:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([C:35]#[C:36][CH:37]2[CH2:41][CH2:40][CH2:39][NH:38]2)=[CH:31][CH:30]=1)=[O:28])[CH3:25].C(Cl)CCl.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([N:38]2[CH2:39][CH2:40][CH2:41][CH:37]2[C:36]#[C:35][C:32]2[CH:33]=[CH:34][C:29]([C:27]([O:26][CH2:24][CH3:25])=[O:28])=[CH:30][CH:31]=2)=[O:23])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 235119142-(2-(4-Ethoxycarbonylphenyl)ethynyl)pyrrolidine

Product 1

HCID 69332958HCID 69332958, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (1.45 g, 4.6 mmol), 2-(2-(4-ethoxycarbonylphenyl)ethynyl)pyrrolidine (1.12 g, 4.6 mmol), EDC 1.32 g (6.9 mmol), DMAP (562 mg, 4.6 mmol) in DMF (20 mL) was stirred overnight. The mixture was poured into 1 N HCl and the solid was collected with suction. The solid was dissolved in CHCl3 and died over MgSO4. After removal of the solvent, the residue was chromatographed on silica-gel with CHCl3—MeOH (100:1, v/v) as eluent to give 2.20 g (89%) ethyl 4-[2-[1-[3-methoxy-4-(N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinyl]ethynyl]benzoate as a white amorphous solid. 1H-NMR (CDCl3) δ1.37-1.41 (3 H, m), 1.94-2.22 (4 H, m), 2.29 (3 H, s), 3.41-3.89 (2 H, m), 3.62 (3 H, s), 3.69 (2 H, s), 4.34-4.40 (2 H, m), 4.72-5.01 (1 H, m), 6.33 (1 H, br s), 6.80-8.06 (12 H, m).

Workup

  1. customthe solid was collected with suction
  2. dissolutionThe solid was dissolved in CHCl3
  3. customAfter removal of the solvent
  4. customthe residue was chromatographed on silica-gel with CHCl3—MeOH (100:1

Sources & evidence

ORD record
ord-40810114ebd0441699d0df394b702cab
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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