Diisopropylethylamine → 3-[4-(2-fluoro-phenyl)-piperazin-1-yl]-6-methyl-2H-pyrrolo[1,2-a]pyrazin-1-one

HRID 77366ノート

反応式

HRID 77366 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14](=[NH:27])[CH2:15][N:16]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]2[C:22]([O:24]CC)=O)[CH2:10][CH2:9]1.C(N(CC)C(C)C)(C)C>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:9][CH2:10][N:11]([C:14]2[NH:27][C:22](=[O:24])[C:17]3[N:16]([C:20]([CH3:21])=[CH:19][CH:18]=3)[CH:15]=2)[CH2:12][CH2:13]1

参加物

4

反応物 2

HCID 81531DiisopropylethylamineHCID 86706665ethyl 1-(2-(4-(2-fluorophenyl)piperazin-1-yl)-2-iminoethyl)-5-methyl-1H-pyrrole-2-carboxylate

生成物 1

HCID 727150423-[4-(2-fluoro-phenyl)-piperazin-1-yl]-6-methyl-2H-pyrrolo[1,2-a]pyrazin-1-one収率 88.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
150 °C

実験手順

A mixture of ethyl 1-(2-(4-(2-fluorophenyl)piperazin-1-yl)-2-iminoethyl)-5-methyl-1H-pyrrole-2-carboxylate (150 mg, 0.4 mmol) and N,N-diisopropylethylamine (1.41 mL, 8 mmol) in tetrahydrofuran (4 mL) was heated at 150° C. in a microwave reactor for 3 h. At this time, the solution was cooled to room temperature. The resulting precipitate was collected by filtration, washed with minimal ethyl acetate and air dried to afford 3-[4-(2-fluoro-phenyl)-piperazin-1-yl]-6-methyl-2H-pyrrolo[1,2-a]pyrazin-1-one (115 mg, 87.5%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.55 (s, 1H), 7.21-7.06 (m, 3H), 7.05-6.96 (m, 1H), 6.73 (d, 1H), 6.53 (s, 1H), 6.26 (d, 1H), 3.15 (s, 8H), 2.26 (s, 3H). LC-MS calcd. for C18H20FN4O [(M+H)+] 327, obsd. 326.9.

後処理

  1. temperatureAt this time, the solution was cooled to room temperature
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with minimal ethyl acetate and air
  4. customdried

出典と根拠

ORDレコード
ord-6e00a63f9aab435db62c526427ee88e7
出典データセット
uspto-grants-2014_09
特許番号
US08841299B2

反応ノート

読み込み中…