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Cyclopropanecarbonyl chloride → N-{[2-(2,6-dioxo(3-piperidyl))-1-oxoisoindolin-4-yl]methyl}cyclopropylcarboxamide

HRID 10065
ノート
印刷プレビュー

反応式

HRID 10065 の反応式
N12CCCN=C1CCCCC2.Cl.[NH2:13][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH2:17][N:18]([CH:25]1[CH2:30][CH2:29][C:28](=[O:31])[NH:27][C:26]1=[O:32])[C:19]2=[O:24].[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1>C(#N)C>[O:32]=[C:26]1[CH:25]([N:18]2[CH2:17][C:16]3[C:20](=[CH:21][CH:22]=[CH:23][C:15]=3[CH2:14][NH:13][C:36]([CH:33]3[CH2:35][CH2:34]3)=[O:37])[C:19]2=[O:24])[CH2:30][CH2:29][C:28](=[O:31])[NH:27]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 219885683-(4-(Aminomethyl)-1-oxoisoindolin-2-yl)piperidine-2,6-dione hydrochloride

生成物 1

HCID 21988521N-{[2-(2,6-dioxo(3-piperidyl))-1-oxoisoindolin-4-yl]methyl}cyclopropylcarboxamide収率 50.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile
溶媒

実験手順

1,8-Diazabicyclo[5,4,0]undec-7-ene (0.7 g, 4.62 mmol) was added to a stirred suspension of 3-[4-(aminomethyl)-1-oxoisoindolin-2-yl]piperidine-2,6-dione hydrochloride (0.65 g, 2.10 mmol) in acetonitrile (50 mL). After stirring for 30 min, cyclopropanecarbonyl chloride (0.24 g, 2.31 mmol) was added. The mixture was stirred at room temperature for 17 hours. The mixture was filtered and the solid was recrystallized from methanol (100 mL) to afford N-{[2-(2,6-dioxo(3-piperidyl))-1-oxoisoindolin-4-yl]methyl}cyclopropylcarboxamide (0.36 g, 50%) as a white solid: mp 262–264° C.; 1H NMR (DMSO-d6) δ 11.02 (s, 1H), 8.63 (t, J=5.7 Hz, 1H), 7.65–7.47 (m, 3H), 5.18–5.11 (dd, J=5.0 and 13.2 Hz, 1H), 4.46 (d=17.3 Hz, 1H), 4.38–4.31 (m, 3H), 3.00–2.85 (m, 1H), 2.65–2.30 (m, 2H), 2.04–1.99 (m, 1H), 1.64–1.54 (m, 1H), 0.69–0.65 (m, 4H); 13C NMR (DMSO-d6) δ 172.82, 172.69, 170.96, 168.03, 140.08, 134.76, 131.66, 130.70, 128.30, 121.64, 51.54, 46.15, 31.16, 22.59, 13.47, 6.27; Anal. Calcd. For C18H19N3O4: C, 63.33; H, 5.61; N, 12.31. Found: C, 62.97; H, 5.55; N, 12.33.

後処理

  1. stirringThe mixture was stirred at room temperature for 17 hours
  2. filtrationThe mixture was filtered
  3. customthe solid was recrystallized from methanol (100 mL)

出典と根拠

ORDレコード
ord-2e0049b47acb409b9843b0b579786509
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07091353B2

反応ノート

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