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

HRID 42806ノート

反応式

HRID 42806 の反応式
N#N.[CH3:3][C:4]1([C:9]2[CH:14]=[C:13]([CH2:15]OS(C)(=O)=O)[CH:12]=[CH:11][N: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:14]=[C:13]([CH2:15][N:26]3[N:25]=[C:24]([N+:21]([O-:23])=[O:22])[CH:28]=[N:27]3)[CH:12]=[CH:11][N:10]=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 86649484Methanesulfonic acid 2-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-4-ylmethyl ester

生成物 1

HCID 673655522-(2-Methyl-[1,3]dioxolan-2-yl)-4-(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 2-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-4-ylmethyl ester (303 mg, 1.11 mmol) in DMF (2.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (115 mg, 1.01 mmol) in DMF (2.0 mL) pre-treated for 30 min with DIPEA (0.35 mL, 2.02 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 (5:1 to 2:1 hept-EA) gave the title compound as a pale yellow oil: TLC:rf (1:2 hept-EA)=0.20. LC-MS-conditions 02: tR=0.77 min, [M+H]+=292.24.

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 (5:1 to 2:1 hept-EA)

出典と根拠

ORDレコード
ord-7ab547e0cb4d4a518b853c5b04aefc86
出典データセット
uspto-grants-2013_09
特許番号
US08536209B2

反応ノート

読み込み中…