Malononitrile → HCID 89647164, 화합물

HRID 531205노트

반응식

HRID 531205 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]=O)=[CH:7][CH:8]=1.[C:11](#[N:15])[CH2:12][C:13]#[N:14].C(N(CC)CC)C.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH2:35][C:34](=[O:36])[N:33]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[N:32]=2)=[CH:27][CH:26]=1>C(O)C>[NH2:14][C:13]1[O:36][C:34]2[N:33]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[N:32]=[C:31]([C:28]3[CH:27]=[CH:26][C:25]([O:24][CH3:23])=[CH:30][CH:29]=3)[C:35]=2[CH:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:12]=1[C:11]#[N:15]

참가 물질

6

반응물 4

HCID 8010MalononitrileHCID 8471TriethylamineHCID 312444-MethoxybenzaldehydeHCID 103081595-(4-Methoxyphenyl)-2-phenyl-2,4-dihydro-3H-pyrazol-3-one

생성물 1

HCID 89647164HCID 89647164, 화합물수율 82%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of anisaldehyde (350 μL, 2.87 mmol, 1.0 equ.), malononitrile (190 mg, 2.87 mmol, 1.0 equ.) and triethylamine (400 μL, 2.87 mmol, 1.0 equ.) in ethanol (10 mL) was stirred for 1 min, followed by the addition of 3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-5(4H)-one (764 mg, 2.87 mmol, 1 equ.). The reaction mixture was concentrated after 24 h and the precipitate was washed with ethanol and hexanes, and then re-crystallized from ethanol to give 6-amino-3,4-bis(4-methoxyphenyl)-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (1.06 g, 2.35 mmol, 82%) as a white solid. 1H-NMR (400 MHz) DMSO: 7.93-7.91 (d, 2H), 7.56-7.52 (m, 4H), 7.38-7.35 (t, 1H), 7.15-7.11 (m, 4H), 6.83-6.78 (m, 4H), 4.98 (s, 1H), 3.70 (s, 3H), 3.66 (s, 3H), 13C-NMR (100 MHz) DMSO: 159.5, 158.9, 158.4, 146.6, 145.5, 137.9, 136.6, 129.8, 129.0, 128.3, 127.0, 125.2, 121.0, 120.4, 114.2, 114.1, 97.7, 60.3, 55.5, 55.3, 37.1; LC/MS-MS: 452.3→89.1 m/z; GS1 and GS2 at 30, DP=36, CE=39, CXP=4, tR=3.47 min.

후처리

  1. concentrationThe reaction mixture was concentrated after 24 h
  2. washthe precipitate was washed with ethanol and hexanes
  3. customre-crystallized from ethanol

출처 및 근거

ORD 기록
ord-23d0381f29e2478ba472a36e1026d4fb
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353121B2

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