Malononitrile → HCID 89647460, compound

HRID 531199Notes

Reaction equation

HRID 531199 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10](#[N:14])[CH2:11][C:12]#[N:13].C(N(CC)CC)C.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH2:34][C:33](=[O:35])[N:32]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:31]=2)=[CH:26][CH:25]=1>C(O)C>[NH2:13][C:12]1[O:35][C:33]2[N:32]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:31]=[C:30]([C:27]3[CH:26]=[CH:25][C:24]([O:23][CH3:22])=[CH:29][CH:28]=3)[C:34]=2[CH:6]([C:5]2[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=2)[C:11]=1[C:10]#[N:14]

Participants

6

Reactant 4

HCID 8010MalononitrileHCID 8471TriethylamineHCID 680234-FluorobenzaldehydeHCID 103081595-(4-Methoxyphenyl)-2-phenyl-2,4-dihydro-3H-pyrazol-3-one

Product 1

HCID 89647460HCID 89647460, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-fluorobenzaldehyde (300 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 precipitate formed was filtered off and washed with ethanol and hexanes, and re-crystallized from ethanol to afford 6-amino-4-(4-fluorophenyl)-3-(4-methoxyphenyl)-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (800 mg, 1.83 mmol, 64%) as white solid. 1H-NMR (400 MHz) DMSO: 7.93-7.91 (d, 2H), 7.55-7.53 (m, 4H), 7.41-7.37 (t, 1H), 7.26-7.23 (m, 4H), 7.07-7.05 (t, 2H), 6.84-6.82 (d, 2H), 5.11 (s, 1H), 3.72 (s, 3H) 13C-NMR (100 MHz) DMSO: 162.6, 159.6, 159.0, 146.6, 145.5, 140.7, 140.6, 137.9, 130.0, 129.9, 129.8, 128.3, 127.1, 125.0, 121.1, 120.2, 115.6, 115.4, 114.1, 97.3, 59.6, 55.5, 37.0; LC/MS-MS: 439.2→373.0 m/z; GS1 and GS2 at 30, DP=61, CE=35, CXP=24, tR=4.28 min.

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered off
  3. washwashed with ethanol and hexanes
  4. customre-crystallized from ethanol

Sources & evidence

ORD record
ord-4699a9a211a6499c8ba964c0325e5333
Source dataset
uspto-grants-2016_05
Patent number
US09353121B2

Reaction notes

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