Hydrazine → 11-(4-Fluorophenyl)-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one

HRID 907961ノート

反応式

HRID 907961 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:17]([C:18]3[N:22]([CH3:23])[N:21]=[CH:20][N:19]=3)[C:16](=O)[C:15]3[C:14]([C:25]([O:27]CC)=O)=[CH:13][CH:12]=[CH:11][C:10]=3[NH:9]2)=[CH:4][CH:3]=1.[NH2:30][NH2:31]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[NH:9][C:10]3[C:15]4[C:16](=[N:30][NH:31][C:25](=[O:27])[C:14]=4[CH:13]=[CH:12][CH:11]=3)[CH:17]2[C:18]2[N:22]([CH3:23])[N:21]=[CH:20][N:19]=2)=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 9321HydrazineHCID 67260599ethyl 2-(4-fluorophenyl)-3-(1-methyl-1H-1,2,4-triazol-5-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

生成物 1

HCID 13618630811-(4-Fluorophenyl)-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one収率 90%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
25 °C

実験手順

A 100 mL round-bottom flask equipped with a thermometer and magnetic stirrer was charged with ethyl 2-(4-fluorophenyl)-3-(1-methyl-1H-1,2,4-triazol-5-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate (1.72 g, 4.4 mmol), methanol (15 mL), and NH2NH2 (4 mL, 85%). The mixture was stirred at 25° C. for 5 hr. The reaction was monitored by HPLC for completion. The mixture was evaporated under reduced pressure and methanol was added to make slurry. The suspension was filtered. The obtained solid was washed with 20 mL of methanol, and was dried to afford the title compound (1.4 g, yield 90%). LC-MS (ESI) m/z: 363 (M+1)+. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 3.65 (s, 3H), 4.93-4.97 (m, 2H), 7.12-7.19 (m, 3H), 7.39-7.43 (m, 2H), 7.47-7.50 (m, 2H), 7.58-7.60 (m, 1H), 7.79 (s, 1H), 12.22 (s, 3H).

後処理

  1. customA 100 mL round-bottom flask equipped with a thermometer and magnetic stirrer
  2. customThe mixture was evaporated under reduced pressure and methanol
  3. additionwas added
  4. filtrationThe suspension was filtered
  5. washThe obtained solid was washed with 20 mL of methanol
  6. customwas dried

出典と根拠

ORDレコード
ord-86439bc17ccc4129ab3704ff4d160583
出典データセット
uspto-grants-2011_09
特許番号
US08012976B2

反応ノート

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