Hydrochloric Acid → HCID 23512371, compound

HRID 354479Notes

Reaction equation

HRID 354479 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].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].CCN(CC)CC.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]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[O:11])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:27]([OH:29])=[O:28])([O-:36])=[O:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 23512494HCID 23512494, compound

Product 1

HCID 23512371HCID 23512371, compoundYield 3%

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 Et3N (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-7006cad4af1a46b9b0ca8c7ab625dac0
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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