Diisopropylethylamine → HCID 58324477、化合物

HRID 69646

反応式

HRID 69646 の反応式
O[CH2:2][C:3]1[CH:14]=[N:13][C:6]2[N:7]([CH3:12])[CH2:8][C:9](=[O:11])[NH:10][C:5]=2[CH:4]=1.[I-].C(C[P+](C)(C)C)#N.C(N(C(C)C)C(C)C)C.Cl.[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([CH:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)=[CH:36][CH:35]=1>C(#N)CC.O>[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([CH:40]2[CH2:41][CH2:42][N:43]([CH2:2][C:3]3[CH:14]=[N:13][C:6]4[N:7]([CH3:12])[CH2:8][C:9](=[O:11])[NH:10][C:5]=4[CH:4]=3)[CH2:44][CH2:45]2)=[CH:36][CH:35]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 27578434-(4-chlorophenyl)piperidine HydrochlorideHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 583244317-(hydroxymethyl)-4-methyl-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

生成物 1

HCID 58324477HCID 58324477、化合物収率 11.1%

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

7-(hydroxymethyl)-4-methyl-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one (85.0 mg, 0.44 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 4-(4-chlorophenyl) piperidine 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 (18.1 mg, 11%) as a white solid. 1H NMR (DMSO-d6) δ (ppm): 10.49 (s, 1H), 7.61 (d, J=2.0 Hz, 1H), 7.30-7.36 (m, 2H), 7.23-7.29 (m, 2H), 6.95 (d, J=2.0 Hz, 1H), 3.92 (s, 2H), 3.32 (s, 3H), 2.84-2.92 (m, 5H), 1.98 (t, J=10.7 Hz, 2H), 1.66-1.75 (m, 2H), 1.50-1.64 (m, 2H). [M+H] calc'd for C20H23ClN4O, 371; found, 371.

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-88c8f19c7d0b473cb9e6de3b5e040b83
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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