Hydrazine → 3-(4-Methylpiperazino)-anilino-5-amino-1,2,4-triazole

HRID 583919

反応式

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11](N=C=S)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[N+]([O-])(O)=O.C[C:22]1C=C(C)[N:24]([C:28]([NH2:30])=[NH:29])[N:23]=1.CC(C)([O-])C.[K+].[NH2:37]N>CS(C)=O>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[NH:37][C:22]2[N:29]=[C:28]([NH2:30])[NH:24][N:23]=2)[CH2:6][CH2:7]1

参加物

反応条件

温度: 55 °C

実験手順

4-(4-Methylpiperazino)-phenyl isothiocyanate was reacted with 1 equivalent of 3,5-dimethylpyrazole-1-carboxamidine nitrate and 1.1 equivalents of potassium t-butoxide in DMSO at 55° C. for 4 hours. 10 equivalents of hydrazine were added and stirred at 55° C. for 4 hrs. Subsequent concentration, dissolution in methanol, filtering of impurities and concentration gave 3-(4-methylpiperazino)-anilino-5-amino-1,2,4-triazole Compound 9A (87% yield). 1H NMR (400 MHz, (CD3)2SO) δ 9.05 (s,1H), 8.60 (s, 1H), 7.35 (d, 2H), 6.77 (d, 2H), 5.70 (s, 2H), 2.97 (m, 4H), 2.48 (m, 4H), 2.23 (s, 3H); MS (ESI) m/z: 274 (M+H+). 3-(4-methylpiperazino)-anilino-5-amino-1,2,4-triazole Compound 9A was acylated with 2,6-difluoro benzoyl chloride Compound 1F in anhydrous pyridine to produce compound 71 (30% yield). 1H NMR (300 MHz, (CD3)2SO) δ 9.07 (s, 1H), 7.88 (s, 1H), 7.72-7.66 (m, 1H), 7.32 (t, 1H), 7.25-7.17 (m, 2H), 6.97-6.92 (m, 1H), 6.71 (d, 1H), 3.39-3.35 (m, 2H), 3.17 (s, 3H), 3.00-2.97 (m, 4H), 2.51-2.46 (m, 4H); MS (ESI) m/z: 414 (M+H+).

後処理

concentrationSubsequent concentration, dissolution in methanol
filtrationfiltering of impurities and concentration

出典と根拠

ORDレコード: ord-05137786b8784b1db8b70f78afdb49b2
出典データセット: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US06924302B2

反応式

参加物

反応物 4

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

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