Triethylamine → 2-(3-Nitropyridin-2-yl)-5-{(2-methoxy-6-methylpyridin-4-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-2,4-dihydro-[1,2,4]triazol-3-one

HRID 1161400ノート

反応式

HRID 1161400 の反応式
[N+:1]([C:4]1[C:5]([NH:10][NH2:11])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(N(CC)CC)C.C[O:20][C:21](=O)[N:22]=[C:23](SC)[C:24]([C:38]1[CH:43]=[C:42]([CH3:44])[N:41]=[C:40]([O:45][CH3:46])[CH:39]=1)=[N:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:36]=[C:35]([CH3:37])[O:34][N:33]=2)=[CH:28][CH:27]=1>CN(C=O)C>[N+:1]([C:4]1[C:5]([N:10]2[C:21](=[O:20])[NH:22][C:23]([CH:24]([C:38]3[CH:43]=[C:42]([CH3:44])[N:41]=[C:40]([O:45][CH3:46])[CH:39]=3)[NH:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]4[N:36]=[C:35]([CH3:37])[O:34][N:33]=4)=[CH:28][CH:27]=3)=[N:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 35789352-Hydrazinyl-3-nitropyridineHCID 72312832{2-(2-Methoxy-6-methylpyridin-4-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

生成物 1

HCID 1363892672-(3-Nitropyridin-2-yl)-5-{(2-methoxy-6-methylpyridin-4-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-2,4-dihydro-[1,2,4]triazol-3-one収率 28.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

After adding 32 mg of (3-nitropyridin-2-yl)hydrazine [CAS No. 15367-16-5] and 29 μl of triethylamine to a solution of 90 mg of {2-(2-methoxy-6-methylpyridin-4-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester in 3 ml of DMF, the mixture was stirred at 85° C. for 16 hours under a nitrogen atmosphere. The reaction mixture was concentrated, and the residue was dissolved in 2 ml of a methanol:THF=1:1 mixed solvent. After adding 42 μl of acetic acid and 64 mg of sodium cyanotrihydroborate to the reaction mixture, it was stirred at room temperature for 4 hours. After filtering the reaction mixture, it was purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give 2-(3-nitropyridin-2-yl)-5-{(2-methoxy-6-methylpyridin-4-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-2,4-dihydro-[1,2,4]triazol-3-one (30 mg).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in 2 ml of a methanol
  3. additionAfter adding 42 μl of acetic acid and 64 mg of sodium cyanotrihydroborate to the reaction mixture, it
  4. filtrationAfter filtering the reaction mixture, it
  5. customwas purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid)

出典と根拠

ORDレコード
ord-9e58f2d3fe2d449994e202b7d1bf0357
出典データセット
uspto-grants-2010_10
特許番号
US07816522B2

反応ノート

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