Methyl 4-Formylbenzoate → 4-(1-Ethyl-5-trifluoromethanesulfonyl-1H-benzoimidazol-2-yl)-benzoic acid methyl ester

HRID 1358761Notes

Reaction equation

HRID 1358761 reaction equation
[CH2:1]([NH:3][C:4]1[C:5]([NH2:17])=[CH:6][C:7]([S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11])=[CH:8][CH:9]=1)[CH3:2].[CH:18]([C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1)=O>C(O)CCCC>[CH3:27][O:26][C:24](=[O:25])[C:23]1[CH:28]=[CH:29][C:20]([C:18]2[N:3]([CH2:1][CH3:2])[C:4]3[CH:9]=[CH:8][C:7]([S:10]([C:13]([F:16])([F:14])[F:15])(=[O:11])=[O:12])=[CH:6][C:5]=3[N:17]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 15294Methyl 4-FormylbenzoateHCID 703518N1-ethyl-4-trifluoromethanesulfonylbenzene-1,2-diamine

Product 1

HCID 99534764-(1-Ethyl-5-trifluoromethanesulfonyl-1H-benzoimidazol-2-yl)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

N1-Ethyl-4-trifluoromethanesulfonyl-benzene-1,2-diamine (134 mg, 0.50 mmol) and methyl 4-formylbenzoate (82 mg, 1.1 equiv) were dissolved in 0.8 mL dry pentanol and heated to reflux for 18 h. The reaction mixture was then evaporated to one-third volume by blowing with a stream of nitrogen while heating. Upon cooling, the solids were collected and washed with ether to yield 155 mg upon drying. The solids may be recrystallized from EtOAc/ether to yield pure ester 35: 1HNMR (400 MHz, d6-DMSO) δ 8.48 (d, J=1.65 Hz, 1H), 8.19 (m, 3H), 8.01 (m, 3H), 4.45 (q, J=7.24 Hz, 2H), 3.92 (s, 3H), 1.36 (t, J=7.22 Hz, 3H); LCMS-APCI in/z 413 [M+1]+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 h
  3. customThe reaction mixture was then evaporated to one-third volume
  4. temperaturewhile heating
  5. temperatureUpon cooling
  6. customthe solids were collected
  7. washwashed with ether
  8. customto yield 155 mg
  9. customupon drying
  10. customThe solids may be recrystallized from EtOAc/ether

Sources & evidence

ORD record
ord-e80552a49e984ee0be17694fd5fb142c
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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