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

HRID 77366

Reaction equation

[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

Participants

Conditions

Temperature: 150 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-6e00a63f9aab435db62c526427ee88e7
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841299B2

Linked notes

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