Diisopropylethylamine → 7-((4-(4-chlorophenyl)piperazin-1-yl)methyl)-4-methyl-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

HRID 716272

반응식

HRID 716272 반응식
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]([N: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:35]=[CH:36][C:37]([N:40]2[CH2:45][CH2:44][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)[CH2:42][CH2:41]2)=[CH:38][CH:39]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 30847201-(4-Chlorophenyl)piperazine HydrochlorideHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 583244317-(hydroxymethyl)-4-methyl-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

생성물 1

HCID 468644427-((4-(4-chlorophenyl)piperazin-1-yl)methyl)-4-methyl-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one수율 9%

시약·촉매·용매 2

HCID 962Water용매HCID 7854Propionitrile용매

반응 조건

온도
90 °C

실험 절차

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 1-(4-chlorophenyl)piperazine hydrochloride (104.8 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 (14.7 mg, 8%) as a white solid. 1H NMR (DMSO-d6) δ (ppm): 10.50 (s, 1H), 7.63 (d, J=1.8 Hz, 1H), 7.21 (d, J=9.1 Hz, 2H), 6.96 (d, J=2.0 Hz, 1H), 6.92 (d, J=9.1 Hz, 2H), 3.93 (s, 2H), 3.34 (s, 2H), 3.10 (br. s., 4H), 2.91 (s, 3H), 2.46 (br. s., 4H). [M+H] calc'd for C19H22ClN5O, 372. found, 372.

후처리

  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

출처 및 근거

ORD 기록
ord-ef7b052b8ff64702b636228b0e06245a
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187497B2

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