1,2-Dichloroethane → HCID 23512537, compound

HRID 354277Notes

Reaction equation

HRID 354277 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:19][C:20]([OH:22])=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][CH:14]=1)=[O:11].[CH2:23]([O:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([C:34]#[C:35][CH:36]2[CH2:40][CH2:39][CH2:38][NH:37]2)=[CH:30][CH:29]=1)=[O:27])[CH3:24].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:19][C:20]([N:37]2[CH2:38][CH2:39][CH2:40][CH:36]2[C:35]#[C:34][C:31]2[CH:32]=[CH:33][C:28]([C:26]([O:25][CH2:23][CH3:24])=[O:27])=[CH:29][CH:30]=2)=[O:22])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:11]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 22244728HCID 22244728, compoundHCID 235119142-(2-(4-Ethoxycarbonylphenyl)ethynyl)pyrrolidine

Product 1

HCID 23512537HCID 23512537, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-methoxy-4-(N′-phenylureido)phenylacetic acid (180 mg, 0.6 mmol), 2-(2-(4-ethoxycarbonylphenyl)ethynyl)pyrrolidine (146 mg, 0.6 mmol), EDC (173 mg, 0.9 mmol), DMAP (73 mg, 0.6 mmol), and cat HOBt in DMF (10 mL) was stirred overnight. The mixture was poured into 1 N HCl and the solid was collected with suction. The residue was dissolved in CHCl3 and dried over MgSO4. After removal of the solvent, the residue was chromatographed on silica-gel with CHCl3—MeOH (10:1, v/v) as eluent to give 192 mg (61%) ethyl 4-[2-[1-[3-methoxy-4-(N′-phenylureido)phenylacetyl]-2-pyrrolidinyl]ethynyl]benzoate as a light yellow amorphous solid. 1H-NMR (CDCl3) δ1.38 (3 H, t, J=6.8 Hz), 1.98-2.24 (4 H, m), 3.48-3.89 (2 H, m), 3.53 (2 H, s), 3.62 (3 H, s), 4.33-4.40 (2 H, m), 4.78-5.04 (1 H, m), 6.77-8.00 (14 H, m).

Workup

  1. customthe solid was collected with suction
  2. dissolutionThe residue 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 (10:1

Sources & evidence

ORD record
ord-cd14843a1cd44f67aa934949028b2400
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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