1,2-Dichloroethane → HCID 69332958, compound

HRID 350340Notes

Reaction equation

HRID 350340 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 dried 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.

Workup

  1. customthe solid was collected with suction
  2. dissolutionThe solid was dissolved in CHCl3
  3. dry with materialdried over MgSO4
  4. customAfter removal of the solvent
  5. customthe residue was chromatographed on silica-gel with CHCl3-MeOH (100:1

Sources & evidence

ORD record
ord-6d01f88c2b54418c9d63fa9bd09d31b3
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

Loading…