Chlorodimethylaluminum → 2-Methyl-4-{[1-(methylsulfonyl)azetidin-3-yl]oxy)-N-(2-methyl-2H-1,2,3-triazol-4-yl)-1-benzofuran-6-carboxamide

HRID 1643772ノート

反応式

HRID 1643772 の反応式
[CH3:1][N:2]1[N:6]=[C:5]([NH2:7])[CH:4]=[N:3]1.[Al](Cl)(C)C.[CH3:12][C:13]1[O:14][C:15]2[CH:21]=[C:20]([C:22](OCC)=[O:23])[CH:19]=[C:18]([O:27][CH:28]3[CH2:31][N:30]([S:32]([CH3:35])(=[O:34])=[O:33])[CH2:29]3)[C:16]=2[CH:17]=1>ClCCl>[CH3:12][C:13]1[O:14][C:15]2[CH:21]=[C:20]([C:22]([NH:7][C:5]3[CH:4]=[N:3][N:2]([CH3:1])[N:6]=3)=[O:23])[CH:19]=[C:18]([O:27][CH:28]3[CH2:31][N:30]([S:32]([CH3:35])(=[O:34])=[O:33])[CH2:29]3)[C:16]=2[CH:17]=1

参加物

5

反応物 3

HCID 79147ChlorodimethylaluminumHCID 145364352-Methyl-2H-1,2,3-triazol-4-amineHCID 59560425Ethyl 2-methyl-4-{[1-(methylsulfonyl)azetidin-3-yl]oxy}-1-benzofuran-6-carboxylate

生成物 1

HCID 595603392-Methyl-4-{[1-(methylsulfonyl)azetidin-3-yl]oxy)-N-(2-methyl-2H-1,2,3-triazol-4-yl)-1-benzofuran-6-carboxamide収率 68.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-methyl-2H-1,2,3-triazol-4-amine (267 mg, 1.98 mmol) in dichloromethane (5 mL) at 0° C. was added Al(CH3)2Cl (1.98 mL, 1.98 mmol, 1M in hexanes) drop-wise. After the addition, the ice-bath was removed, and the mixture was stirred for 30 minutes at room temperature. Ethyl 2-methyl-4-{[1-(methylsulfonyl)azetidin-3-yl]oxy}-1-benzofuran-6-carboxylate (70 mg, 0.198 mmol) was added and the stirring was continued for 14 h. The reaction was quenched with potassium sodium tartrate tetrahydrate (20% w/w) cautiously. The product was extracted with CH2Cl2, washed with brine and dried over Na2SO4. The product was purified by gradient silica gel chromatography using CHCl3/MeOH (95/5 to 85/15) to give the title compound (55 mg, 68%) as a white solid after evaporation of the solvents. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.51 (s, 3 H) 2.94 (s, 3 H) 4.06-4.15 (m, 3 H) 4.16 (d, J=4.80 Hz, 2 H) 4.39 (dd, J=9.60, 6.32 Hz, 2 H) 5.05-5.23 (m, 1 H) 6.54 (s, 1 H) 6.97 (s, 1 H) 7.54 (s, 1 H) 8.12 (s, 1 H) 8.46 (s, 1 H); MS (ESI, pos): 406.

後処理

  1. additionAfter the addition
  2. customthe ice-bath was removed
  3. waitthe stirring was continued for 14 h
  4. customThe reaction was quenched with potassium sodium tartrate tetrahydrate (20% w/w) cautiously
  5. extractionThe product was extracted with CH2Cl2
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. customThe product was purified by gradient silica gel chromatography

出典と根拠

ORDレコード
ord-e8cfbf7877224090b38facc38eb101c4
出典データセット
uspto-grants-2012_02
特許番号
US08119624B2

反応ノート

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