1-Hydroxybenzotriazole → ethyl 4-[3-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl-N-methylamino]-1-propyl]benzoate

HRID 350547Notes

Reaction equation

HRID 350547 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].[CH3:24][NH:25][CH2:26][CH2:27][CH2:28][C:29]1[CH:39]=[CH:38][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][CH:30]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([N:25]([CH2:26][CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:38][CH:39]=2)[CH3:24])=[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

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 23512152Ethyl 4-(3-methylamino-1-propyl)benzoate

Product 1

HCID 23512235ethyl 4-[3-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl-N-methylamino]-1-propyl]benzoateYield 71%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (456 mg, 1.45 mmol) and ethyl 4-(3-methylamino-1-propyl)benzoate (220 mg, 1.45 mmol) were added EDC.HCl (417 mg, 2.16 mmol), HOBt (cat.), and DMAP (catalytic amount) in DMF (10 mL), and the resulting mixture was stirred overnight. The mixture was diluted with EtOAc (300 mL), washed with brine, dried over MgSO4, and evaporated. The residue was chromatographed on silica-gel with CHCl3-EtOH (10:1) to give 503 mg (71%) ethyl 4-[3-[3-methoxy-4-[N′-(2-methylphenyl) ureido]phenylacetyl-N-methylamino]-1-propyl]benzoate as a yellow oil. MS (FAB) m/z 518(M+H)+.

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was chromatographed on silica-gel with CHCl3-EtOH (10:1)

Sources & evidence

ORD record
ord-0db9ed8ad01f4452af160c39107ebd7d
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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