Hydrochloric Acid → HCID 69332277, compound

HRID 350541Notes

Reaction equation

HRID 350541 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]C1C=CC=CC=1C)=[O:11].C[C:25]1[C:33]([N+:34]([O-:36])=[O:35])=[C:32]([O:37][CH2:38][CH2:39][NH2:40])[CH:31]=[CH:30][C:26]=1[C:27]([OH:29])=[O:28].Cl>CN(C=O)C>[N+:34]([C:33]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[O:37][CH2:38][CH2:39][NH:40][C:21](=[O:23])[CH2:20][C:5]1[CH:6]=[CH:7][C:8]([N:9]([C:4]2[CH:3]=[CH:8][CH:7]=[CH:6][C:5]=2[CH3:20])[C:10]([NH2:12])=[O:11])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:27]([OH:29])=[O:28])([O-:36])=[O:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 23512494HCID 23512494, compound

Product 1

HCID 69332277HCID 69332277, compoundYield 5.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of pentafluorophenyl ester of 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (1.86 g, 3.87 mmol) and methyl 3-nitro-4-(2-aminoethoxy)benzoic acid (0.93 g, 3.87 mmol) in DMF (27 mL) was added Et3 N (0.90 mL, 6.46 mmol), and the resulting mixture was stirred overnight. The mixture was poured into 0.5 N HCl and the resulting solid was collected. The crude solid was dissolved in THF-0.25 N NaOH (1/1, 20 mL) and the resulting mixture was heated under reflux overnight. The mixture was extracted with EtOAc, washed with brine, dried over Na2SO4, and evaporated. The crude solid was recrystallized from CHCl3-EtOH to give 60 mg (3% for 2 steps) 3-nitro-4-[2-[3-methoxy-4-[N-(2-methylphenyl)ureido]phenylacetyl]aminoethoxy]benzoic acid 257 as a yellow crystalline solid. mp 112–115° C.; 1H-NMR (DMSO-d6) d 2.24 (s, 3 H), 3.37–3.66 (m, 7 H), 3.84 (s, 3 H), 4.27–4.30 (m, 1 H), 6.74–8.56 (series of m, total 12 H); MS (FAB) m/z 523 (M++1); Anal. Calcd for C26H26N4O8.3/2H2O: C, 56.83; H, 5.32; N, 10.20. Found: C, 56.66; H, 4.90; N, 9.33.

Workup

  1. customthe resulting solid was collected
  2. dissolutionThe crude solid was dissolved in THF-0.25 N NaOH (1/1, 20 mL)
  3. temperaturethe resulting mixture was heated
  4. temperatureunder reflux overnight
  5. extractionThe mixture was extracted with EtOAc
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. customThe crude solid was recrystallized from CHCl3-EtOH

Sources & evidence

ORD record
ord-79d7277c64914e63a2494a6acb850001
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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