Acetonitrile → HCID 11409618, compound

HRID 2222233Notes

Reaction equation

HRID 2222233 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2C(=C[CH:11]=1)N=[C:7]([CH2:12][N:13]1[C:21]([C:22]3[N:26]([CH3:27])[CH:25]=[C:24]([C:28]#[N:29])[CH:23]=3)=[C:20]3[C:15]([N:16]([CH2:32][CH:33]4[CH2:35][CH2:34]4)[C:17](=[O:31])[NH:18][C:19]3=S)=[N:14]1)[CH:6]=[CH:5]2.[CH:36]([NH:38][NH2:39])=O.[C:40](#[N:42])[CH3:41]>[Hg](Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:42]=[CH:40][CH:41]=[C:7]2[CH2:12][N:13]1[C:21]([C:22]2[N:26]([CH3:27])[CH:25]=[C:24]([C:28]#[N:29])[CH:23]=2)=[C:20]2[C:19]3[N:18]([CH:36]=[N:38][N:39]=3)[C:17](=[O:31])[N:16]([CH2:32][CH:33]3[CH2:34][CH2:35]3)[C:15]2=[N:14]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 12229HydrazinecarboxaldehydeHCID 86608961HCID 86608961, compound

Product 1

HCID 11409618HCID 11409618, compound

Reagents, catalysts & solvents 1

HCID 24085Mercuric ChlorideCatalyst

Procedure

To a solution of 5-[2-[(6-chloroquinolinyl)methyl]-7-(cyclopropylmethyl)-6-oxo-4-thioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]-1-methyl- 1H-pyrrole-3-carbonitrile (0.14 g) in acetonitrile (5 mL) and formic hydrazide (80 mg) was added mercury(II) chloride (160 mg). After stirring overnight at rt, the reaction was warmed (Tb=70 C). After 5 h with heat, the reaction was filtered through a celite bed and concentrated. The residue was purified by flash chromatography using a FlashMaster™ yielding 44 mg, 1H NMR (300 MHz, CHLOROFORM-D) d ppm 0.57 (m, 4H) 1.48 (m, J=10.93 Hz, 1H) 3.45 (s, 3H) 4.15 (t, J=6.59 Hz, 2H) 5.86 (m, 2H) 6.68 (d, J=1.70 Hz, 1H) 6.83 (d, J=4.52 Hz, 1H) 7.40 (d, J=1.70 Hz, 1H) 7.72 (dd, J=8.95, 2.17 Hz, 1H) 7.88 (d, J=2.07 Hz, 1H) 8.13 (d, J=8.85 Hz, 1H) 8.84 (d, J=4.33 Hz, 1H) 8.93 (s, 1H);

Workup

  1. temperaturethe reaction was warmed (Tb=70 C)
  2. temperatureAfter 5 h with heat
  3. filtrationthe reaction was filtered through a celite bed
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. customyielding 44 mg, 1H NMR (300 MHz, CHLOROFORM-D) d ppm 0.57 (m, 4H) 1.48 (m, J=10.93 Hz, 1H) 3.45 (s, 3H) 4.15 (t, J=6.59 Hz, 2H) 5.86 (m, 2H) 6.68 (d, J=1.70 Hz, 1H) 6.83 (d, J=4.52 Hz, 1H) 7.40 (d, J=1.70 Hz, 1H) 7.72 (dd, J=8.95, 2.17 Hz, 1H) 7.88 (d, J=2.07 Hz, 1H) 8.13 (d, J=8.85 Hz, 1H) 8.84 (d, J=4.33 Hz, 1H) 8.93 (s, 1H)

Sources & evidence

ORD record
ord-1c6d00b61200478c97479f80cc41fb3d
Source dataset
uspto-grants-2008_05
Patent number
US07371757B2

Reaction notes

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