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

HRID 77366노트

반응식

HRID 77366 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
150 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6e00a63f9aab435db62c526427ee88e7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841299B2

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