Benzaldehyde → HCID 89649860, 화합물

HRID 531193노트

반응식

HRID 531193 반응식
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](#[N:13])[CH2:10][C:11]#[N:12].C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH2:33][C:32](=[O:34])[N:31]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:30]=2)=[CH:25][CH:24]=1>C(O)C>[NH2:12][C:11]1[O:34][C:32]2[N:31]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:30]=[C:29]([C:26]3[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[CH:28][CH:27]=3)[C:33]=2[CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]=1[C:9]#[N:13]

참가 물질

6

반응물 4

HCID 240BenzaldehydeHCID 8010MalononitrileHCID 8471TriethylamineHCID 103081595-(4-Methoxyphenyl)-2-phenyl-2,4-dihydro-3H-pyrazol-3-one

생성물 1

HCID 89649860HCID 89649860, 화합물수율 58%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of benzaldehyde (290 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 19 h and washed with ethanol and hexanes, re-crystallized from ethanol, and washed with hexanes and ethanol to give 6-amino-3-(4-methoxyphenyl)-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (695 mg, 1.65 mmol, 58%) as a white solid. 1H-NMR (400 MHz) DMSO: 7.94-7.92 (d, 2H), 7.58-7.53 (m, 2H), 7.41-7.37 (t, 1H), 7.27-7.16 (m, 7H), 6.83-6.81 (d, 2H), 5.04 (s, 1H), 3.71 (s, 3H), 13C-NMR (100 MHz) DMSO: 159.5, 159.0, 146.6, 145.6, 144.5, 137.9, 129.8, 128.9, 128.3, 128.0, 127.3, 127.1, 125.1, 121.1, 120.3, 114.1, 97.5, 59.8, 55.5, 37.9; LC/MS-MS: 421.2→355.0 m/z; GS1 and GS2 at 30, DP=71, CE=33, CXP=24, tR=4.28 min.

후처리

  1. concentrationThe reaction mixture was concentrated after 19 h
  2. washwashed with ethanol and hexanes
  3. customre-crystallized from ethanol
  4. washwashed with hexanes and ethanol

출처 및 근거

ORD 기록
ord-1ca565cfb68b4fd08243243a0ad2b3f7
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353121B2

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