Diisopropylethylamine → HCID 46864443、化合物

HRID 69651

反応式

HRID 69651 の反応式
[CH2:1]([N:8]1[CH2:13][C:12](=[O:14])[NH:11][C:10]2[CH:15]=[C:16]([CH2:19]O)[CH:17]=[N:18][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].C(C[P+](C)(C)C)#N.C(N(C(C)C)C(C)C)C.Cl.[Cl:39][C:40]1[CH:45]=[CH:44][C:43]([N:46]2[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)=[CH:42][CH:41]=1>C(#N)CC.O>[CH2:1]([N:8]1[CH2:13][C:12](=[O:14])[NH:11][C:10]2[CH:15]=[C:16]([CH2:19][N:49]3[CH2:48][CH2:47][N:46]([C:43]4[CH:42]=[CH:41][C:40]([Cl:39])=[CH:45][CH:44]=4)[CH2:51][CH2:50]3)[CH:17]=[N:18][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 30847201-(4-Chlorophenyl)piperazine HydrochlorideHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 583244634-benzyl-7-(hydroxymethyl)-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

生成物 1

HCID 46864443HCID 46864443、化合物収率 40.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 7854Propionitrile溶媒

反応条件

温度
90 °C

実験手順

4-benzyl-7-(hydroxymethyl)-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one (100 mg, 0.37 mmol) was suspended in propionitrile (1 mL) and (cyanomethyl)trimethylphosphonium iodide (123.0 mg, 0.51 mmol) was added followed by N-ethyl-N-isopropylpropan-2-amine (180 ul, 1.03 mmol). To the stirred mixture was then added 1-(4-chlorophenyl)piperazine hydrochloride (104.5 mg, 0.45 mmol). The reaction was heated to 90° C. with stirring for 2 h. The reaction was then cooled to room temperature and diluted with water (3 mL) and filtered. The solids were collected and refluxed in ethanol (5 mL) for 1 h. The suspension was cooled back to room temperature and filtered. The precipitate was filtered off and dried in vacuum to afford the title compound (66.6 mg, 40%) as a white solid. 1H NMR (DMSO-d6) δ (ppm): 10.57 (s, 1H), 7.64 (d, J=1.8 Hz, 1H), 7.33 (d, J=4.5 Hz, 4H), 7.25-7.30 (m, 1H), 7.19-7.24 (m, 2H), 7.01 (d, J=1.8 Hz, 1H), 6.92 (d, J=9.1 Hz, 2H), 4.72 (s, 2H), 3.86 (s, 2H), 3.36 (s, 2H), 3.07-3.15 (m, 4H), 2.44-2.49 (m, 4H). [M+H] calc'd for C25H26ClN5O, 448; found, 448.

後処理

  1. temperatureThe reaction was then cooled to room temperature
  2. filtrationfiltered
  3. customThe solids were collected
  4. temperaturerefluxed in ethanol (5 mL) for 1 h
  5. temperatureThe suspension was cooled back to room temperature
  6. filtrationfiltered
  7. filtrationThe precipitate was filtered off
  8. customdried in vacuum

出典と根拠

ORDレコード
ord-5bb20f10cdef4c5687f2b0f876d1984f
出典データセット
uspto-grants-2014_09
特許番号
US08822470B2

関連ノート

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