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

HRID 1358761

反応式

HRID 1358761 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 62761-Pentanol溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-e80552a49e984ee0be17694fd5fb142c
出典データセット
uspto-grants-2003_07
特許番号
US06596772B1

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