Hydrazine hydrate (1:1) → HCID 58792211, compound

HRID 2222234Notes

Reaction equation

HRID 2222234 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]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:15]([N:16]([CH2:32][CH:33]3[CH2:35][CH2:34]3)[C:17](=[O:31])[NH:18][C:19]2=S)=[N:14]1.O.[NH2:37][NH2:38]>C1COCC1.O.C(OCC)(=O)C.[Hg]Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]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:15]([N:16]([CH2:32][CH:33]3[CH2:35][CH2:34]3)[C:17](=[O:31])[N:18]=[C:19]2[NH:37][NH2:38])=[N:14]1

Participants

7

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 100289915-[2-[(6-chloroquinolin-4-yl)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

Product 1

HCID 58792211HCID 58792211, compound

Reagents, catalysts & solvents 4

HCID 24182Mercurous ChlorideCatalyst2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[2-[(6-chloroquinolin-4-yl)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 (0.24 g) in THF (5 mL) were added hydrazine hydrate (0.30 mL) and mercury chloride (0.30 g). After 4 h, a second addition of hydrazine hydrate (0.20 mL) and mercury chloride (0.30 g) was done. After stirring overnight, the mixture was diluted with water and ethyl acetate. The mixture was then filtered through a celite bed. The organic solution was collected, washed with saturated NaHCO3 and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography using a FlashMaster™ yielding 0.18 g.

Workup

  1. filtrationThe mixture was then filtered through a celite bed
  2. customThe organic solution was collected
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. customyielding 0.18 g

Sources & evidence

ORD record
ord-66c742cb1a5949f89b6ac2fd39d5a0f9
Source dataset
uspto-grants-2008_05
Patent number
US07371757B2

Reaction notes

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