Nitrogen → 2-(2-Methyl-[1,3]dioxolan-2-yl)-6-(4-nitro-[1,2,3]triazol-2-ylmethyl)-pyridine

HRID 42786

反応式

HRID 42786 の反応式
N#N.[CH3:3][C:4]1([C:9]2[N:14]=[C:13]([CH2:15]OS(C)(=O)=O)[CH:12]=[CH:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.[N+:21]([C:24]1[CH:28]=[N:27][NH:26][N:25]=1)([O-:23])=[O:22].CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[CH3:3][C:4]1([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([CH2:15][N:26]3[N:25]=[C:24]([N+:21]([O-:23])=[O:22])[CH:28]=[N:27]3)[N:14]=2)[O:5][CH2:6][CH2:7][O:8]1

参加物

8

反応物 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 2781504-nitro-2H-1,2,3-triazoleHCID 86649482Methanesulfonic acid 6-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-ylmethyl ester

生成物 1

HCID 673654742-(2-Methyl-[1,3]dioxolan-2-yl)-6-(4-nitro-[1,2,3]triazol-2-ylmethyl)-pyridine

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methanesulfonic acid 6-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-ylmethyl ester (164 mg, 0.6 mmol) in DMF (2.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (57 mg, 0.5 mmol) in DMF (1.0 mL) pre-treated for 30 min with DIPEA (0.20 mL, 1.17 mmol) and the reaction mixture was stirred for 48 h at 50° C. Water (10 mL), followed by EA (10 mL) were added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (4:1 to 1:1 hept-EA) gave the title compound as a pale yellow oil: TLC:rf (1:1 hept-EA)=0.50. LC-MS-conditions 02: tR=0.90 min, [M+H]+=292.35.

後処理

  1. additionwere added
  2. extractionThe aq. layer was extracted with EA (10 mL)
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (4:1 to 1:1 hept-EA)

出典と根拠

ORDレコード
ord-8a3e03d2364f443ebcc2de91fd55fb59
出典データセット
uspto-grants-2013_09
特許番号
US08536209B2

関連ノート

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