Piperazine → 9-Hydroxy-4-phenyl-6-[3-(1-piperazinyl)propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11095ノート

反応式

HRID 11095 の反応式
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]3[C:24](=[O:28])[NH:25][C:26](=[O:27])[C:13]=3[C:12]=2[C:11]2[CH:10]=[C:9]([OH:29])[CH:8]=[CH:7][C:6]1=2.[NH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>>[OH:29][C:9]1[CH:8]=[CH:7][C:6]2[N:5]([CH2:4][CH2:3][CH2:2][N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[C:17]3[CH:16]=[C:15]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:14]4[C:24](=[O:28])[NH:25][C:26](=[O:27])[C:13]=4[C:12]=3[C:11]=2[CH:10]=1

参加物

3

反応物 2

HCID 4837PiperazineHCID 867602016-(3-Bromopropyl)-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

生成物 1

HCID 219804049-Hydroxy-4-phenyl-6-[3-(1-piperazinyl)propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione収率 55%

実験手順

Bromide (204) (70 mg, 0.16 mmol) prepared as described in example 173 was reacted with piperazine according to The procedure described in example 179 except that the reaction was performed at room temperature for 20 h, to give amine (215) (40 mg, 55%) as a yellow powder, mp 178–183° C. 1H NMR δ [(CD3)2SO] 11.0 (br s, 1H), 9.35 (br s, 1H), 8.40 (d, J=2.4 Hz, 1H), 7.78 (s, 1H), 7.62 (m, 2H), 7.56 (d, J=8.8 Hz, 1H), 7.45 (m, 3H), 7.14 (dd, J=8.8, 2.4 Hz, 1H), 4.49 (t, J=6.3 Hz, 2H), 2.52 (m, 4H), 2.12 (m, 6H), 1.91 (m, 2H). Found: C, 69.31; H, 5.97; N, 11.49. C27H26N4O3.4/5H2O requires: C, 69.16; H, 5.93; N, 11.94.

出典と根拠

ORDレコード
ord-2a3230ac66084754a1ba89fe21f7b805
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

反応ノート

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