Ammonia → 2-Chloro-5-phenylpyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 2170175ノート

反応式

HRID 2170175 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]2=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:10]=[CH:11][N:4]2[N:3]=1.[NH3:18]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH2:18])[C:5]2=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:10]=[CH:11][N:4]2[N:3]=1

参加物

4

反応物 2

HCID 222AmmoniaHCID 90386287HCID 90386287、化合物

生成物 1

HCID 903863842-Chloro-5-phenylpyrrolo[2,1-f][1,2,4]triazin-4-amine収率 64.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2,4-dichloro-5-phenylpyrrolo[2,1-f][1,2,4]triazine (0.500 g, 1.89 mmol) in THF (5 mL), NH3 gas was bubbled at −20° C. for 15 min. The reaction mixture was stirred at RT for 1 h. The reaction mixture was concentrated under reduced pressure to remove THF and water (30 mL) was added to the resulting residue. The aqueous solution was extracted with EtOAc (3×100 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by CombiFlash (REDISEP®, silica gel, 40 g, 45% EtOAc/petroleum ether) to afford 2-chloro-5-phenylpyrrolo[2,1-f][1,2,4]triazin-4-amine (0.300 g, 64.8%). LCMS Condition B-81: retention time 2.14 min, [M+1]=245.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 5.98 (br s, 1H), 6.75 (d, J=2.4 Hz, 1H), 7.38-7.43 (m, 2H), 7.46-7.52 (m, 3H), 7.80 (d, J=2.4 Hz, 1H), 8.40 (br s, 1H).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove THF and water (30 mL)
  3. additionwas added to the resulting residue
  4. extractionThe aqueous solution was extracted with EtOAc (3×100 mL)
  5. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by CombiFlash (REDISEP®, silica gel, 40 g, 45% EtOAc/petroleum ether)

出典と根拠

ORDレコード
ord-fb1bab48f2cf49e4a8ecc4526e0304b6
出典データセット
uspto-grants-2015_06
特許番号
US09050345B2

反応ノート

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