HCID 23511825, compound → methyl 4-[N-[1-[3-methoxy-4-[N'-(2-fluorophenyl)ureido]phenylacetyl]-2-pyrrolidinyl methyl]-N-methylamino]-3-nitrobenzoate

HRID 350397Notes

Reaction equation

HRID 350397 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[F:19])=[O:11].[N+:24]([C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][C:36]=1[N:37]([CH2:39][CH:40]1[CH2:44][CH2:43][CH2:42][NH:41]1)[CH3:38])[C:30]([O:32][CH3:33])=[O:31])([O-:26])=[O:25]>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOCC.C1C=CC2N(O)N=NC=2C=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([N:41]2[CH2:42][CH2:43][CH2:44][CH:40]2[CH2:39][N:37]([C:36]2[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][C:27]=2[N+:24]([O-:26])=[O:25])[CH3:38])=[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[F:19])=[O:11]

Participants

7

Reactant 2

HCID 23511825HCID 23511825, compoundHCID 23511932methyl 3-nitro-4-[N-(2-pyrrolidinyl)methyl-N-methylamino]benzoate

Product 1

HCID 69332166methyl 4-[N-[1-[3-methoxy-4-[N'-(2-fluorophenyl)ureido]phenylacetyl]-2-pyrrolidinyl methyl]-N-methylamino]-3-nitrobenzoateYield 105.5%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 757711-HydroxybenzotriazoleCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-methoxy-4-[N′-(2-fluorophenyl)ureido]phenylacetic acid (630.0 mg, 1.979 mmol), methyl 3-nitro-4-[N-(2-pyrrolidinyl)methyl-N-methylamino]benzoate (553.0 mg, 1.885 mmol), EDC(Hydrochloride) (542.0 mg, 2.827 mmol), HOBt (25.5 mg, 0.189 mmol), and DMAP (23.1 mg, 0.189 mmol) in DMF (5.0 mL) was stirred at room temp. for 2 hr. The mixture was diluted with Et2O, washed with brine, and dried over Na2SO4. The solvent was removed under a reduced pressure, and the residue was chromatographed on silica-gel with CHCl3-MeOH (30:1, v/v) as eluent to afford 1.18 g (100%) methyl 4-[N-[1-[3-methoxy4-[N′-(2-fluorophenyl)ureido]phenylacetyl]-2-pyrrolidinyl methyl]-N-methylamino]-3-nitrobenzoate as a yellow foam, which is used to the subsequent reaction without further purification.

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed under a reduced pressure
  4. customthe residue was chromatographed on silica-gel with CHCl3-MeOH (30:1

Sources & evidence

ORD record
ord-fb623a385acd471e8992840f936a25a5
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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